CAS: 5989-54-8; (S)-1-Methyl-4-(Prop-1-En-2-yl)Cyclohex-1-Ene

该化合物是单环单体,分子式为C10H16,自然地成为豪华轿车的对等分子,其特性为不同的柑橘芳香,通常见于柑橘水果的基本油类中,其纯度和稳定性较高,适合在香味,调味和工业过程中用作溶剂,其性能也有利于用于不对称合成和作为生产特殊化学品的前体. (-)-Limonene因其毒性低和生物降解性而具有价值,符合环境意识的配方.

结构式图片

相似化合物

495-61-4 18031-40-8 591-49-1

欧盟法规

统一分类与标签欧盟化妆品法规附录三-限用物质清单压力设备指令-第1组危险流体REACH注册ECHA物质欧盟气雾剂指令-标签制度工作场所安全标识要求ECHA物质C&L通报REACH预注册废弃物危险特性清单

上下游产品

CAS号86851-45-8 (R)-(+)-binapht... | CAS号25996-10-5 (Z)-1-bromo-3,7... | CAS号106-25-2 橙花醇 | CAS号7785-70-8 蒎烯 | CAS号18172-67-3 β-蒎烯 | CAS号7785-26-4 (1S)-(-)-α-蒎烯 | CAS号78-79-5 异戊二烯 | CAS号175522-76-6 (R,E)-(2,2-dime... | CAS号136476-12-5 (S,E)-(2-methyl... | CAS号99-49-0 L-香芹酮 | CAS号1195-32-0 4-异丙烯基甲苯 | CAS号308363-12-4 (R)-香芹醇 | CAS号18031-40-8 (-)-紫苏醛 | CAS号1197-07-5 (1R,5S)-rel-香芹醇 | CAS号1197-06-4 2-Cyclohexen-1-... | CAS号32543-51-4 cis-(S)-(-)-lim... | CAS号42477-94-1 cis-(S)-4-Isopr... | CAS号99-48-9 L-香芹醇,顺反异构体混合物

合成工艺路线路线简述

  • 合成目标产物 (S)-(-)-Limonene 主要起始原料 Geranyl Pyrophosphate Ammonium 200
  • (文献来源)合成步骤主要原料 Geranyl Pyrophosphate Ammonium 200
📜橙花醇置于四氯化锡,三苯基膦,偶氮二甲酸二乙酯体系中,用 四氢呋喃,二氯甲烷 作为反应溶剂,化学反应 18.0H,反应生成 (S)-(-)-柠檬烯
参考文献:路易斯酸活化的手性离去基团:手性烯烃的对映选择性亲电加成.
标题:路易斯酸活化的手性离去基团:手性烯烃的对映选择性亲电加成.
摘要:已经开发了一种使用binol衍生物作为手性离去基团和路易斯酸的新策略,用于前手性烯烃的对映选择性烷基化.已证明(R)-2,2'-双[2-(三甲基甲硅烷基)乙氧基甲基]-1,1'-联苯酚是用于甲硅烷基烯醇醚和三取代烯烃的对映选择性羟甲基化的有效试剂.前手性烯烃的亲电加成伴随着乙缩醛的裂解,该缩醛被sncl4双重激活,并且硅通过s(n)2取代过程产生了δ效应.使用该策略还描述了环状萜烯的对映选择性合成.
DOI:10.1021/jo020165L

海关参考信息

专利信息


专利号:US-11926589-B2
优先权日:2019-07-09
标 题 :Process for the synthesis of non-racemic cyclohexenes
发明人:REISMAN SARAH; ROMBOLA MICHAEL; LADD CAROLYN L; MCLAUGHLIN MARTIN JOHN; ZUEND STEPHAN; GOETZ ROLAND
权利人:BASF CORP; CALIFORNIA INST OF TECHN
摘要:This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M m+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R 10a , R 10b , R 10c , R 10d , R 10a′ , R 10b′ , R 10c′ , R 10d′ , Z and Z′ have the meanings as defined in the description.

专利号:US-6423877-B1
优先权日:1999-11-15
标题:Synthesis of pseudopterosin compounds
发明人:COREY ELIAS J
权利人:HARVARD COLLEGE
摘要:The present invention is directed to a new synthetic route to pseudopterosin aglycone (3): n a key intermediate for the synthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and E (2). The pathway of synthesis starts with the abundant and inexpensive (S)-(−)-limonene and its long-known cyclic hydroboration product (4) and leads to the chiral hydroxy ketone (6). Conversion of (6) to (10) followed by a novel aromatic annulation produced (15) which underwent highly diastereoselective cyclization to afford the protected pseudopterosin aglycone (16). The naturally occurring pseudopterosins such as (1) and (2) are readily available from this key intermediate.

专利号:US-3676506-A
优先权日:1969-12-29
标题:Synthesis of novel compounds useful for production of juvabione
发明人:CRAWFORD ROBERT J
权利人:PROCTER & GAMBLE
摘要:Disclosed herein are processes for the production of 6-methyl-2(4-methylcyclohex-3-en-1-yl)hept-1-en-4-ol and 2-methyl-6-(4methylcyclohex-3-en-1-yl)heptan-4-ol using metalated limonene as the starting reactant. The novel compounds of the invention are useful in the synthesis of juvabione, a product having juvenile hormone activity.

专利号:WO-2024042405-A1
优先权日:2022-08-26
标 题:Compositions and methods for the synthesis of bio-based polymers
发明人:OLIVEIRA ANA; CAPÊTO ANA PAULA; PINTADO MANUELA
权利人:AMYRIS BIO PRODUCTS PORTUGAL UNIPESSOAL LTDA; UNIV CATOLICA PORTUGUESA
摘要:The present disclosure provides compositions and methods for the synthesis of bio-based polymers (e.g., polyurethanes and polyesters) from secondary materials produced during a fermentation process. The disclosure also features intermediates produced during these processes, as well as compositions containing the same.

专利号:US-12234203-B2
优先权日:2020-03-12
标 题:Process for the synthesis of cannabidiol and intermediates thereof
发明人:ANAND RADHIKA; SHARMA SUMIT; SINGH CHAM PANKAJ; GANNEDI VEERANJANEYULU; KUMAR MUKESH; PRATAP SINGH VARUN; PRAKASH RAHUL VISHAV; ASREY VISHWAKARMA RAM; PAL SINGH PARVINDER
权利人:COUNCIL OF SCIENT AND INDUSTRIAL RESEARCH AN INDIAN REGISTERED BODY INCORPORATED UNDER THE REGN OF T; COUNCIL OF SCIENT AND INDUSTRIAL RESEARCH AN INDIAN REGISTERED BODY INCORPORATED UNDER THE REGN OF S
摘要:The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.

专利号:US-3676505-A
优先权日:1969-12-29
标 题:4-(4-methylcyclohex-3-en-1-yl)pent-4-en-1-ol and a process for its synthesis
发明人:CRAWFORD ROBERT J
权利人:PROCTER & GAMBLE
摘要:Disclosed herein is the synthesis of 4-(4-methylcyclohex-3-en-1yl)pent-4-en-1-ol, a novel compound useful as a starting reagent for the production of lanceol and lanceal, known perfume materials. Limonene is first metalated and then reacted with ethylene oxide to give the novel compound. This compound can then be converted to a known aldehyde which can be used to produce lanceol and lanceal by known processes.

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品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

合成参考文献


摘要:Kantchev, E. A. B.; Organ, M. G., Science of Synthesis, (2009) 48, 10.
摘要:Matsumoto, K.; Katsuki, T.; Arends, I. W. C. E., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 99.
摘要:Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 317.
摘要:Liu, G.; Chen, P., Science of Synthesis: Catalytic Transformations via CH Activation, (2015) 2, 17.
摘要:Xia, F.; Ye, S., Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016) 2, 28.
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