(-)-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.
• Facile and efficient synthesis of chiral sulfoxide esters: Versatile tool in asymmetric synthesis
  作者：Reshma Nagpal、Aman Bhalla、Jitender Bhalla、Shamsher S. Bari、Renu Thapar

  DOI：10.1080/00397911.2018.1554145

  日期：2019.1.17

  Abstract Facile and efficient synthesis of sulfoxide esters using menthols as chiral auxiliary is described. Phenylthio/benzylthio/naphthylthioacetic esters act as an efficient substrate for chiral sulfoxides via oxidation in one step. The structural and stereochemical aspects of target product were established on the basis of various spectroscopic studies, namely FT-IR, NMR (1H NMR and 13C NMR) and

  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