(R)-2-Phenylsulfanyl-propionaldehyde | 125660-37-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-2-Phenylsulfanyl-propionaldehyde
• 英文别名: (2R)-2-phenylsulfanylpropanal
• CAS: 125660-37-9
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: YQORRZVFWPFOOV-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Phenylsulfanyl-propionaldehyde 在 palladium on activated charcoal 2,2,6,6-tetramethylpiperidinyl-lithium 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 甲苯 为溶剂， 反应 76.0h， 生成 (4aR,5S,8R,8aS)-5-Methoxymethoxy-8-((R)-1-phenylsulfanyl-ethyl)-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  无环手性烷氧基二烯的Diels-Alder反应：氧与硫为烯丙基导向基团

  摘要：

  在纯手性diense的Diels-Alder反应的面部选择性1和2 N-苯基马来酰亚胺的：使用三个亲二烯体进行探测（5一），苯醌（5 b）和4-苯基-1,2,4-三唑啉-3,5-二酮（5 c）。

  DOI：

  10.1016/s0040-4039(00)99278-5
• 作为产物：
  描述：

  methyl (R)-(+)-2-(phenylthio)propanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (R)-2-Phenylsulfanyl-propionaldehyde
  参考文献：
  名称：

  Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched N-tert-Butyloxycarbonyl (Boc)-Protected N-Allylamines

  摘要：

  Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN(3)) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples), Whereas the reaction is well suited for the transformation of alpha-unbranched sulfides to a-branched sulfenamides, the enantiomerically pure alpha-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% eel. A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of alpha-branched amines that bear a secondary allyl substituent (five examples, 71-93% yield). This method failed for the alpha-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)(3)/NEt3 in CH2Cl2 (three examples, 43-62% yield).

  DOI：

  10.1021/jo991569p

文献信息

• Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched <i>N</i>-<i>tert</i>-Butyloxycarbonyl (Boc)-Protected <i>N</i>-Allylamines
  作者：Thorsten Bach、Christina Körber

  DOI：10.1021/jo991569p

  日期：2000.4.1

  Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN(3)) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples), Whereas the reaction is well suited for the transformation of alpha-unbranched sulfides to a-branched sulfenamides, the enantiomerically pure alpha-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% eel. A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of alpha-branched amines that bear a secondary allyl substituent (five examples, 71-93% yield). This method failed for the alpha-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)(3)/NEt3 in CH2Cl2 (three examples, 43-62% yield).
• Diels-Alder reactions of acyclic chiral alkoxy dienes: Oxygen versus sulfur as an allylic directing group
  作者：Patrick G. McDougal、Joseph M. Jump、Christian Rojas、Joseph G. Rico

  DOI：10.1016/s0040-4039(00)99278-5

  日期：1989.1

  Facial selectivity in the Diels-Alder reaction of homochiral diense1and2was probed using three dienophiles: N-phenylmaleimide (5a), benzoquinone (5b) and 4-phenyl-1,2,4-triazoline-3,5-dione (5c).

  在纯手性diense的Diels-Alder反应的面部选择性1和2 N-苯基马来酰亚胺的：使用三个亲二烯体进行探测（5一），苯醌（5 b）和4-苯基-1,2,4-三唑啉-3,5-二酮（5 c）。