(+)-(1S,2R)-2-methyl-<2-(4-methyl-3-pentenyl)cyclopropyl>methanol | 185064-36-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1S,2R)-2-methyl-<2-(4-methyl-3-pentenyl)cyclopropyl>methanol
• 英文别名: [(1S,2S)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl]methanol；(+)-(2S,3S)-2,3-methano-3,7-dimethyl-6-octen-1-ol；[(1S,2S)-2-Methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl]methanol
• CAS: 185064-36-2
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: XVBJCXHXYYFQKZ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  香叶醇 、 Zn(CH₂I)₂*DME 在 chiral dioxaborolane derivative 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到(+)-(1S,2R)-2-methyl-<2-(4-methyl-3-pentenyl)cyclopropyl>methanol
  参考文献：
  名称：

  多烯的化学和对映选择性环丙烷化：基于手性助剂和手性试剂的方法

  摘要：

  使用衍生自二氧杂硼烷的试剂研究了含有其他烯烃的烯丙基醇的化学和对映选择性环丙烷化。如果将手性二氧杂硼烷配体/烯丙醇的混合物用Zn（CH 2 I）2 · DME络合物溶液处理，通常观察到较高的化学和对映选择性。

  DOI：

  10.1016/0040-4039(96)01798-4

文献信息

• Enantioselective Cyclopropanation of Allylic Alcohols with Dioxaborolane Ligands:  Scope and Synthetic Applications
  作者：André B. Charette、Hélène Juteau、Hélène Lebel、Carmela Molinaro

  DOI：10.1021/ja982055v

  日期：1998.11.1

  the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also

  已发现一种非常有效的手性控制剂，可使用双（碘甲基）锌将烯丙醇转化为相应的富含对映异构体的环丙烷。根据该方法可以获得多种手性、非外消旋环丙基甲醇。该方法成功地扩展到非共轭和共轭多烯和高烯丙醇的环丙烷化。烯丙基氨基甲酸酯的环丙烷化也已用该系统进行了研究，但发现富含对映体的环丙基甲基胺最好由富含对映体的环丙基甲醇制备。
• Cyclopropanated Aromachemicals
  申请人：Turin Luca

  公开号：US20070259042A1

  公开（公告）日：2007-11-08

  A compound of formula (I): wherein R is —CH 2 OH, —C(O)H, —C(OR 3 ) 2 H, —C(OR 4 )(OH)H, —CH═NC 6 H 4 C(O)OR 5 or —CH═NR 6 ; R 1 and R 2 are each independently H or CH 3 ; R 3 and R 4 are each independently H or a straight or branched aliphatic group having from 1 to 12 carbon atoms, or each R 3 is covalently linked to the other R 3 to form a cyclic acetal having from 1 to 4 carbon atoms; R 5 is H or a straight or branched aliphatic group, or a cyclic, heterocyclic or aromatic group having from 1 to 12 carbon atoms; and R 6 has at least 10 carbon atoms and is an aliphatic group or an aromatic group. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavouring and in articles of manufacture is also provided.

  化合物的式子为（I）：其中R为—CH2OH，—C（O）H，—C（OR3）2H，—C（OR4）（OH）H，—CH═NC6H4C（O）OR5或—CH═NR6; R1和R2各自独立地为H或CH3; R3和R4各自独立地为H或具有1至12个碳原子的直链或支链脂肪基，或每个R3与另一个R3共价连接以形成具有1至4个碳原子的环状缩醛; R5为H或直链或支链脂肪基，或具有1至12个碳原子的环状，杂环或芳香族基; 而R6至少有10个碳原子，是脂肪族基或芳香族基。还提供了这些化合物的混合物，其制备方法，其用作香料材料以应用于各种基质以及其在调味和制造物品中的使用。
• Aromachemicals
  申请人：Turin Luca

  公开号：US20070276152A1

  公开（公告）日：2007-11-29

  A compound or mixture of compounds of formulae: wherein R 1 and R 2 are each independently H or CH 3 .

  一个化学式为的化合物或混合物：其中R1和R2分别独立地为H或CH3。
• Asymmetric Simmons–Smith Reaction of Allylic Alcohols with Al Lewis Acid/N Lewis Base Bifunctional Al(Salalen) Catalyst
  作者：Hiroaki Shitama、Tsutomu Katsuki

  DOI：10.1002/anie.200705641

  日期：2008.3.14
• Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol
  作者：Hiroki Asao、Hiroyuki Sakauchi、Shigefumi Kuwahara、Hiromasa Kiyota

  DOI：10.1016/j.tetasy.2007.02.007

  日期：2007.3

  Both enantiomers of cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol were synthesized and their odor properties evaluated. Odor characters in enantiomeric pairs were similar in the geraniol series. The (+)-(2R,3S)-nerol derivative showed various odor aspects. From the results of nor-leaf alcohol derivatives, an interaction between the (2-re,3-re)-face of nor-leaf alcohol and the human olfactory receptor was suggested. The odor of (3R)-matsutake alcohol derivative was superior to the enantiomer. (c) 2007 Elsevier Ltd. All rights reserved.