2-((benzyloxy)methyl)thiirane | 16495-22-0

• 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: 2-((benzyloxy)methyl)thiirane
• 英文别名: (R)-2-Benzyloxymethyl-thiirane；(2R)-2-(phenylmethoxymethyl)thiirane
• CAS: 16495-22-0
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: XTTQPPURFZRJDU-SNVBAGLBSA-N

物化性质

• 沸点：
  271.8±13.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((benzyloxy)methyl)thiirane 在 lithium aluminium tetrahydride 作用下， 生成 (S)-1-benzyloxy-propane-2-thiol
  参考文献：
  名称：

  二硫醇。第二十三部分。2,3-二巯基丙醇和相关硫醇的旋光形式

  摘要：

  描述了由1,2- O-异亚丙基甘油通过苄基2,3-环氧-丙基醚新合成2,3-二巯基丙醇。按照类似的路线，已经通过（S）-1,2- O-异亚丙基甘油通过（S）-苄基2,3-环氧丙基醚合成了（R）-2,3-二巯基丙醇。通过其他途径，（S）-1,2 - O-异亚丙基甘油也通过（R）-苄基2,3-环氧丙醚被（i）转化为（S）-2,3-二巯基丙醇，（ii）。 ）通过（R）-2,3-异丙基二烯二氧基丙基硫醇乙酸酯转化为（R）-3-巯基丙烷-1,2-二醇，和（iii）通过（将R）-苄基2，3-表硫丙基醚转化为（S）-2-巯基丙醇。

  DOI：

  10.1039/j39670001021
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 SC(NH₂)2 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 2-((benzyloxy)methyl)thiirane
  参考文献：
  名称：

  Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

  摘要：

  The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92%, e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)(4)] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)(2)] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by P-31 NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)(2)] gave the enantiomenc complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00143-x

文献信息

• Biocatalytic Thionation of Epoxides for Enantioselective Synthesis of Thiiranes
  作者：Ran Ma、Xia Hua、Cheng‐Li He、Hui‐Hui Wang、Zhu‐Xiang Wang、Bao‐Dong Cui、Wen‐Yong Han、Yong‐Zheng Chen、Nan‐Wei Wan

  DOI：10.1002/anie.202212589

  日期：2022.12.23

  A biocatalytic thionation method is presented for the enantioselective synthesis of thiiranes from epoxides by a halohydrin dehalogenase catalyzed kinetic resolution approach using thiocyanate as a sulfur donor. Various chiral thiiranes bearing aryl and alkyl substituents were synthesized in good yields and enantioselectivities by using recombinant Escherichia coli cells expressing the engineered halohydrin

  提出了一种生物催化硫代化方法，用于使用硫氰酸盐作为硫供体，通过卤代醇脱卤酶催化的动力学拆分方法，从环氧化物中对映选择性合成硫杂环丙烷。通过使用表达工程化卤代醇脱卤素酶 HHDHapb 变体的重组大肠杆菌细胞，以良好的产率和对映体选择性合成了带有芳基和烷基取代基的各种手性硫杂环丙烷。
• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• Dithiols. Part XXIII. Optically active forms of 2,3-dimercaptopropanol and related thiols
  作者：A. K. M. Anisuzzaman、L. N. Owen

  DOI：10.1039/j39670001021

  日期：——

  A new synthesis of 2,3-dimercaptopropanol, from 1,2-O-isopropylideneglycerol, by way of benzyl 2,3-epoxy-propyl ether, is described. Following a similar route, (R)-2,3-dimercaptopropanol has been synthesised from (S)-1,2-O-isopropylideneglycerol through (S)-benzyl 2,3-epoxypropyl ether. By other routes, (S)-1,2-O-iso-propylideneglycerol is also converted (i) through (R)-benzyl 2,3-epoxypropyl ether

  描述了由1,2- O-异亚丙基甘油通过苄基2,3-环氧-丙基醚新合成2,3-二巯基丙醇。按照类似的路线，已经通过（S）-1,2- O-异亚丙基甘油通过（S）-苄基2,3-环氧丙基醚合成了（R）-2,3-二巯基丙醇。通过其他途径，（S）-1,2 - O-异亚丙基甘油也通过（R）-苄基2,3-环氧丙醚被（i）转化为（S）-2,3-二巯基丙醇，（ii）。 ）通过（R）-2,3-异丙基二烯二氧基丙基硫醇乙酸酯转化为（R）-3-巯基丙烷-1,2-二醇，和（iii）通过（将R）-苄基2，3-表硫丙基醚转化为（S）-2-巯基丙醇。
• Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes
  作者：Nuria Brugat、Josep Duran、Alfonso Polo、Julio Real、Ángel Álvarez-Larena、J.Francesc Piniella

  DOI：10.1016/s0957-4166(02)00143-x

  日期：2002.4

  The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92%, e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)(4)] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)(2)] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by P-31 NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)(2)] gave the enantiomenc complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. (C) 2002 Elsevier Science Ltd. All rights reserved.