(-)-Menthyl α-phenylsulfenyl acetate | 170502-11-1

• 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: (-)-Menthyl α-phenylsulfenyl acetate
• 英文别名: phenylsulfanyl-acetic acid 2'-isopropyl-5'-methyl-cyclohexyl ester；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-phenylsulfanylacetate
• CAS: 170502-11-1
• 化学式: C₁₈H₂₆O₂S
• 分子量: 306.469
• InChiKey: FUWJRNSYBBTJPX-HYVNUMGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-Menthyl α-phenylsulfenyl acetate 在 磺酰氯 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 Phenyl-phenylsulfanyl-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation using chiral α-acyl-α-chloromethylsulphides

  摘要：

  Lewis acid catalysed stereoselective Friedel-Crafts alkylation of aromatic compounds with alpha-(-)-menthyl-oxycarbonyl-alpha-(phenylthio)methyl chloride and alpha-(-)-8-phenylmenthyloxycarbonyl-alpha-(phenylthio)methyl chloride is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00186-5
• 作为产物：
  描述：

  L-薄荷醇 、 苯硫基乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以59%的产率得到(-)-Menthyl α-phenylsulfenyl acetate
  参考文献：
  名称：

  手性亚砜酯的简便高效合成：不对称合成中的多功能工具

  摘要：

  摘要 描述了使用薄荷醇作为手性助剂的亚砜酯的简便高效合成。苯硫基/苄硫基/萘硫基乙酸酯通过一步氧化作用作为手性亚砜的有效底物。目标产物的结构和立体化学方面建立在各种光谱研究的基础上，即 FT-IR、NMR（1H NMR 和 13C NMR）和元素分析。这种方法简单、快速、方便且非常有效。图形概要

  DOI：

  10.1080/00397911.2018.1554145

文献信息

• Electrolytic partial fluorination of organic compounds. Part 15. Stereochemical study of the anodic monofluorination of α-phenylsulfenyl acetates
  作者：Satoru Narizuka、Hiroshi Koshiyama、Akinori Konno、Toshio Fuchigami

  DOI：10.1016/0022-1139(94)03207-g

  日期：1995.7

  The diastereoselective anodic fluorination of α-phenylsulfenyl esters by intramolecular asymmetry-induction has been studied using chiral auxiliaries such as phenethyl, bornyl, isobornyl, menthyl and 8-phenylmenthyl groups. Of these chiral auxiliaries, the 8-phenylmenthyl group gave the best diastereoselectivity. The diastereoselectivity was also affected by supporting electrolytes and it was found

  使用手性助剂如苯乙基，冰片基，异冰片基，薄荷基和8-苯基薄荷基，研究了分子内不对称诱导的α-苯基亚磺酰基酯的非对映选择性阳极氟化。在这些手性助剂中，8-苯基薄荷基具有最佳的非对映选择性。非对映选择性也受支持电解质的影响，发现与Et 3 N·3HF和Et 3 N·2HF相比，Et 4 NF·3HF表现出更好的选择性。
• Asymmetric aromatic vicarious nucleophilic substitution of hydrogen
  作者：Mark D. Drew、David A. Jackson、Nicholas J. Lawrence、John Liddle、Robin G. Pritchard

  DOI：10.1039/a606921e

  日期：——

  A series of novel one-pot aromatic vicarious nucleophilic substitution of hydrogen/asymmetric alkylation reactions are described; the enolates of several chiral cyclohexyl phenylsulfanylacetates react readily with 3-chloronitrobenzene followed by subsequent stereoselective alkylation.

  介绍了一系列新颖的一锅式芳香族代亲核取代氢/不对称烷基化反应；几种手性环己基苯硫基乙酸酯的烯醇化物很容易与 3-氯硝基苯发生反应，随后发生立体选择性烷基化反应。
• Pummerer-type α-functionalization of arylseleninylacetates by treating with trimethylsilyl- or tri-n-butylstannyl-masked nucleophiles and trifluoroacetic anhydride or a Lewis acid
  作者：Kazuaki Shimada、Yutaka Kikuta、Hiroyuki Koganebuchi、Fumi Yonezawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1016/s0040-4039(00)00681-x

  日期：2000.6

  Arylseleninylacetates underwent facile alpha-functionalization on treatment with trimethylsilyl- or tri-n-butylstannyl-masked nucleophiles and trifluoroacetic anhydride (TFAA) or a Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF ARYL CYCLOHEXANE ESTER DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS
  申请人：The Procter & Gamble Company

  公开号：US20190276389A1

  公开（公告）日：2019-09-12

  Personal care compositions, such as oral care and skin care compositions containing a flavor/perfume system comprising one or more coolants. The pleasant cool sensation provided by a coolant is enhanced in terms of quicker onset, greater intensity, impact or longer duration, which improves appeal and acceptability of the compositions to consumers.