(S)-2-((S)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1-phenyl-ethanol | 212965-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-((S)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1-phenyl-ethanol
• 英文别名: (1S)-2-[(2S)-2-hydroxy-2-phenylethyl]sulfanyl-1-phenylethanol
• CAS: 212965-33-8
• 化学式: C₁₆H₁₈O₂S
• 分子量: 274.384
• InChiKey: UXXFFFKLKFFDHH-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1-phenyl-ethanol 在 氯化亚砜 、 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 rac-bis-1,2-(ethylsulfanyl)-1-phenylethane
  参考文献：
  名称：

  Synthesis of C 2 -symmetric tris-thioethers via optically active mustards

  摘要：

  Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are activated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give optically active mustard gas analogues. These compounds serve as substrates for stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00006-0
• 作为产物：
  描述：

  (S)-(+)-1-苯基-1,2-乙二醇对甲苯磺酸酯 在 sodium sulfide 作用下， 以 丙酮 为溶剂， 以82%的产率得到(S)-2-((S)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1-phenyl-ethanol
  参考文献：
  名称：

  手性，对映体纯的硫二甘醇和二甘醇的新型合成

  摘要：

  天然α-羟基酸已经按照O-保护，还原，O-活化，硫醚和醚形成和脱保护的顺序转化为手性，非外消旋的β，β'-二羟基硫醚1a，1b和醚1c。总体收率极好（75％）。为了合成相应的衍生自扁桃酸1，3-二氧戊环衍生物7的二羟基醚1d。

  DOI：

  10.1016/s0957-4166(98)00224-9

文献信息

• Synthesis of oxathiane and morpholine from acyclic precursors: a modified Mitsunobu reaction
  作者：Nidhin Paul、Selvam Kaladevi、Arockiam Jesin Beneto、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1016/j.tet.2012.06.029

  日期：2012.8

  Synthesis of a set of isomeric 2,4,6-triarylmorpholines and 2,6-diaryloxathianes from the corresponding 1,5-diols has been described. The method provides an efficient route to six-membered heterocycles from acyclic diols and is found to be better than Mitsunobu procedure in yield and waste management. In a related study, the ring contraction of pyranone to two isomeric cyclopentenone derivatives through

  已经描述了由相应的1，5-二醇合成一组异构的2，4，6-三芳基吗啉和2，6-二芳基氧杂蒽。该方法提供了从无环二醇到六元杂环的有效途径，发现在产率和废物管理方面比Mitsunobu方法更好。在相关研究中，已经注意到通过纳扎罗夫反应将吡喃酮环收缩成两个异构的环戊烯酮衍生物。
• Stereocontrol between Remote Atom Centers in Acyclic Substrates. Anti Addition of Hydride to 1,5-, 1,6-, and 1,7-Hydroxy Ketones
  作者：Han-Cheng Zhang、Bruce D. Harris、Michael J. Costanzo、Edward C. Lawson、Cynthia A. Maryanoff、Bruce E. Maryanoff

  DOI：10.1021/jo981341m

  日期：1998.10.1

  For conformationally unconstrained, acyclic organic compounds, the control of stereogenic centers at remote positions of a chain, that is, at a distance of four or more atom centers, remains a challenging problem in asymmetric synthesis. We report on our studies of 1,5, 1,6, and 1,7 diastereoselectivity in hydride reductions of acyclic hydroxy amino ketones and related compounds, which were sparked by our discovery of high 1,5 diastereocontrol (>10:1) with substrates such as 17 and 23. We have been able to achieve both high 1,5- and 1,6-anti diastereocontrol in the reduction of 1,5- and 1,6-hydroxy ketone substrates, respectively. However, the level of 1,7-anti diastereocontrol with 1,7-hydroxy ketones was only moderate. More specifically, reduction of 23 to 24 with R-alpine-hydride or Zn(BH4)(2) in CH2Cl2 (predominantly) at -78 degrees C gave high 1,5-anti stereoselectivity (anti/syn = 10:1 or 13:1, respectively), and reduction of 34 to 35 with R-alpine-hydride (CH2Cl2) gave high 1,6-anti selectivity (anti/syn = 12:1, respectively), whereas reduction of 46 to 44 with R-alpine-hydride (CH2Cl2) gave only moderate 1,7-anti stereoselectivity (anti/syn = 3:1). Results for reductions of 1,5- and 1,6-hydroxy ketone substrates having the N-benzyl structural subunit replaced (i.e., 27 --> 28, 29 --> 30, 31 --> 32, 52 --> 53, 54a --> 55a, 54b --> 55b, 54c --> 55c, and 56 --> 57) clearly indicate that the stereoelectronic character of this subunit plays a critical. role in the attainment of high anti asymmetric induction. Thus, while we obtained exceptionally high 1,6-anti stereoselectivity in the reduction of the N-mesitylmethyl substrate, 54c, to 1,6-diols 55c (anti/syn = 22:1) with R-alpine-hydride at -78 degrees C in CH2Cl2, the N-methyl substrate, 54b, gave a relatively modest anti/syn ratio of 3:1. The diminished anti/syn ratio of 4:1 in the R-alpine-hydride reduction of methoxy amino ketone 50 to 51 also indicates the importance of the free hydroxyl group for attaining high 1,6-anti stereoselectivity. To rationalize the high remote anti stereocontrol in such acyclic systems, we discuss a chelation-controlled mechanism, involving external hydride addition to a bicyclic metal complex with a coordinated ketone carbonyl (e.g., 33) vs internal hydride addition to a monocyclic metal complex with an uncoordinated ketone carbonyl (e.g., 58).
• Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1016/s0957-4166(98)00224-9

  日期：1998.7

  converted in a sequence of O-protection, reduction, O-activation, thioether and ether formation and deprotection to chiral, non-racemic β,β′-dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1,3-dioxolane derivatives 7 were obtained.

  天然α-羟基酸已经按照O-保护，还原，O-活化，硫醚和醚形成和脱保护的顺序转化为手性，非外消旋的β，β'-二羟基硫醚1a，1b和醚1c。总体收率极好（75％）。为了合成相应的衍生自扁桃酸1，3-二氧戊环衍生物7的二羟基醚1d。
• Synthesis of C 2 -symmetric tris-thioethers via optically active mustards
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1016/s0040-4020(01)00006-0

  日期：2001.2

  Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are activated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give optically active mustard gas analogues. These compounds serve as substrates for stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.