(1S,3S,4R)-menthyl chloroacetate | 7377-98-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3S,4R)-menthyl chloroacetate
• 英文别名: (+)-menthyl chloroacetate；d-menthyl chloroacetate；(1S,2R,5S)-2-Isopropyl-5-methylcyclohexyl 2-chloroacetate；[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] 2-chloroacetate
• CAS: 7377-98-2；21758-29-2；27994-88-3；88644-14-8；106916-72-7；111957-92-7
• 化学式: C₁₂H₂₁ClO₂
• 分子量: 232.751
• InChiKey: XHQPKRVACXDVNV-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R)-menthyl chloroacetate 在 ammonium hydroxide 、 溶剂黄146 、 亚硝酸异戊酯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 d-menthyl diazoacetate
  参考文献：
  名称：

  Semicorrin金属络合物作为对映选择性催化剂。第2部分。手性（半corrinato）铜配合物催化重氮化合物与烯烃形成对映选择性环丙烷†

  摘要：

  发现手性，C 2对称半corrin配体的铜配合物是从烯烃与重氮化合物形成环丙烷的有效催化剂。在催化剂的1％模式下，重氮乙酸烷基酯与末端烯烃如苯乙烯，丁二烯和1-庚烯平稳地反应，得到相应的光学活性环丙烷羧酸衍生物（表1方案2）。使用其中一种催化剂，对映选择性高达97％ee （表2）。通常，该反应使用双（准corrinato）铜（II）配合物作为预催化剂进行。为了生产活性催化剂，必须首先通过在重氮乙酸酯存在下加热或通过苯肼处理来活化这些配合物。使用由叔丁醇铜（I）原位制备的（semicorrinato）铜（I）配合物进行的实验（方案4）表明，实际的催化剂是[单（semicorrinarinato）]铜（I）。

  DOI：

  10.1002/hlca.19880710621
• 作为产物：
  描述：

  D-薄荷醇 、 氯乙酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (1S,3S,4R)-menthyl chloroacetate
  参考文献：
  名称：

  A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids

  摘要：

  Co)Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC 3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.

  DOI：

  10.1016/s0040-4039(00)61614-3

文献信息

• Synthesis and Antihypertensive Activity of 3-Acetoxy-2,3-dihydro-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (Diltiazem) Derivatives Having Substituents at the 8 Position.
  作者：Hiroaki YANAGISAWA、Koichi FUJIMOTO、Yasuo SHIMOJI、Takuro KANAZAKI、Kanako MIZUTARI、Hiroshi NISHINO、Hiroshi SHIGA、Hiroyuki KOIKE

  DOI：10.1248/cpb.40.2055

  日期：——

  In order to improve the potency and duration of biological actions of diltiazem, a number of 1, 5-benzothiazepine derivatives having the substituents at the 8 position were prepared and evaluated for their antihypertensive activity in spontaneously hypertensive rats. The introduction of methyl, ethyl, isopropyl, benzyl, methoxy, ethoxy, phenoxy, and methylthio groups increased the antihypertensive activity and prolonged duration of action, whereas cyclohexyl, cyclopentoxy, tolyloxy, p-methoxyphenoxy and phenylthio derivatives were less active than diltiazem. Among them, the 8-benzyl and phenoxy derivatives showed the most potent and long-lasting antihypertensive action.

  为了改善地尔硫卓的药效和生物作用持续时间，我们制备了一些在 8 位上具有取代基的 1，5-苯并硫氮杂卓衍生物，并对其在自发性高血压大鼠体内的抗高血压活性进行了评估。甲基、乙基、异丙基、苄基、甲氧基、乙氧基、苯氧基和甲硫基的引入增加了抗高血压活性并延长了作用时间，而环己基、环戊基、甲苯基、对甲氧基苯氧基和苯硫基衍生物的活性低于地尔硫卓。其中，8-苄基和苯氧基衍生物的降压作用最强且持续时间最长。
• Double asymmetric synthesis: Palladium chiral complexes in the alkylation of chiral schiff bases derived from glycine.
  作者：J.P. Genet、N. Kopola、S. Juge、J. Ruiz-Montes、O.A.C. Antunes、S. Tanier

  DOI：10.1016/s0040-4039(00)94713-0

  日期：1990.1

  A new double asymmetric induction in carbon-carbon bond formation is achieved by the use of palladium chiral complexes in the alkylation of chiral Schiff bases derived from glycine. High diastereoisomeric excesses are obtained (90–99%) using N,N-cyclohexylsulfamoylisobornyl derivatives and DIOP as a matched pair.

  通过在衍生自甘氨酸的手性席夫碱的烷基化中使用钯手性络合物，实现了碳-碳键形成的新的双不对称诱导。使用N，N-环己基氨磺酰基酰基冰片基衍生物和DIOP作为配对，可以获得较高的非对映异构体过量（90-99％）。
• Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters
  作者：Hélène Dentel、Isabelle Chataigner、Jean-François Lohier、Mihaela Gulea

  DOI：10.1016/j.tet.2012.01.039

  日期：2012.3

  Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.
• Use of optically active clausenamides for the preparation of pharmaceutical compositions, pharmaceutical compositions containing the same
  申请人：INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP1348696B1

  公开（公告）日：2012-02-01
• Er, Mustafa; Coskun, Necdet, Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 2, p. 198 - 208
  作者：Er, Mustafa、Coskun, Necdet

  DOI：——

  日期：——