(-)-(1S,2R)-2-ethylcyclopropylmethanol | 31915-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1S,2R)-2-ethylcyclopropylmethanol
• 英文别名: (1S,2R)-(-)-2-ethylcyclopropylmethanol；(-)-(2S,3R)-2,3-methano-1-pentanol；cis-2-Ethylcyclopropanemethanol；[(1S,2R)-2-ethylcyclopropyl]methanol
• CAS: 31915-75-0
• 化学式: C₆H₁₂O
• 分子量: 100.161
• InChiKey: BGKKZLRPGJYFIP-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-丁基-1,3,2-二氧硼戊环-4S,5S-二羧酸双(二甲氨基化合物) 、 反-2-戊烯-1-醇 以90%的产率得到
  参考文献：
  名称：

  Charette Andre B., Juteau Helene, J. Amer. Chem. Soc, 116 (1994) N 6, S 2651-2652

  摘要：

  DOI：

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。
• Highly Enantioselective Oxidation of <i>cis</i>-Cyclopropylmethanols to Corresponding Aldehydes Catalyzed by Chloroperoxidase
  作者：Shanghui Hu、Jonathan S. Dordick

  DOI：10.1021/jo016161i

  日期：2002.1.1

  catalyzes the enantioselective oxidation of cyclopropylmethanols. This finding enables a novel route to the synthesis of optically active cyclopropane derivatives, which occur widely in natural products and compounds of pharmaceutical interest. In addition, chiral cyclopropane molecules may be useful model substrates to investigate reaction mechanisms of CPO and the related cytochromes P450.

  氯过氧化物酶（CPO）使用叔丁基氢过氧化物作为末端氧化剂，催化环丙基甲醇（例如2-甲基环丙基甲醇）的对映选择性氧化为环丙基醛。在所有情况下，尽管CPO对两种异构体都具有相似的催化活性，但顺式环丙烷的CPO氧化显示出比反式异构体高得多的对映选择性。这是血红素酶催化环丙基甲醇对映选择性氧化的第一个例子。该发现为光学活性环丙烷衍生物的合成提供了一条新途径，该化合物广泛存在于天然产物和具有药物意义的化合物中。此外，手性环丙烷分子可能是研究CPO与相关细胞色素P450反应机理的有用模型底物。
• Design of Amphoteric Bifunctional Ligands: Application to the Enantioselective Simmons-Smith Cyclopropanation of Allylic Alcohols
  作者：Andre B. Charette、Helene Juteau

  DOI：10.1021/ja00085a068

  日期：1994.3
• 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.
• Charette Andre B., Juteau Helene, J. Amer. Chem. Soc, 116 (1994) N 6, S 2651-2652
  作者：Charette Andre B., Juteau Helene

  DOI：——

  日期：——