tert-butyl(2,2-diphenylvinyl)sulfane | 131589-78-1

• 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: tert-butyl(2,2-diphenylvinyl)sulfane
• 英文别名: (2-Tert-butylsulfanyl-1-phenylethenyl)benzene
• CAS: 131589-78-1
• 化学式: C₁₈H₂₀S
• 分子量: 268.423
• InChiKey: MTULXURHOZEZKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-nitro-1-(phenylthio)-2,2-diphenylethylene 、 potassium 2-methyl-2-propanethiolate 以 二甲基亚砜 为溶剂， 反应 23.0h， 以88%的产率得到tert-butyl(2,2-diphenylvinyl)sulfane
  参考文献：
  名称：

  Addition, substitution and deoxygenation reactions of .alpha.-phenyl-.beta.-nitrostyrenes with the anions of thiols and diethyl phosphite: formation of indoles by reaction with ethyl phosphites

  摘要：

  Reactions of excess RS- (R = Ph, t-Bu) with Ph2C = C(SPh)NO2 in Me2SO form Ph2C = CHSR via conversion of the initial Micheal-type adducts into Ph2C(SR)CH = NO2- and Ph2C = CHNO2. In a similar fashion, reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 forms initially mainly PhSP(O) (OEt)2 and PH2C[P(O)(OEt)2]CH = NO2-, which upon acidic workup will yield the nitroalkane or the Nef reaction product, Ph2C[P(O)(OEt)2]CHO. The reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 also produces Ph2C[P(O)(OEt)2] C = N via a perkow-type reaction of the Michael adduct to yield Ph2C[P(O)(OEt)2]CH = N(O)OP(O)(OEt)2 as an intermediate. The nitrile is also formed from Ph2C[P(O)(OEt)2]CH(NO2)2 with (EtO)2PO- in (EtO)2P(O)H or Me2SO at 30-degrees-C and in > 95% yield by the reaction of (EtO)3P with Ph2C[P(O)(OEt)2CH(NO2)2 at 150-degrees-C. Reaction of Ph2C = CHNO2 or Ph2C[P(O)(OEt)2]CH2NO2 with excess (EtO)2PO- in Me2SO or (EtO)2P(O)H forms 3-(diethoxyphosphinyl)-2,2-diphenylaziridine by a process postulated to involve Ph2C = CHN(O-)OP(O)(OEt)2, Ph2C = CHNOP(O)(OEt)2-, and 2,2-diphenyl-2H-azirine. Similarly, Ph2C = C(SBu-t)NO2 and (EtO)2PO- give 3-(tert-butylthio)-2,2-diphenyl-2H-azirine in Me2SO or 2-(tert-butylthio)-3-phenylindole in (EtO)2P(O)H solution. Deoxygenation of Ph2C = C(X)NO2 to form the 2-X-3-phenylindoles occurs in high yield at 150-degrees-C in (EtO)3P with X = H, PhS, or t-BuS while 2-nitro-3-phenylindole is formed from Ph2C = C(NO2)2 in (EtO)2P(O)H at 150-degrees-C.

  DOI：

  10.1021/jo00002a032

文献信息

• Arylboronic Acid Deborylation Deuteration via Synergistic Thiol, Lewis Base, and Photoredox Catalysis
  作者：Jianyang Dong、Mo Yu、Fuyang Yue、Hongjian Song、Yuxiu Liu、Linan Wu、Duanyun Si、Cheng Yang、Guang Yang、Qingmin Wang

  DOI：10.1021/acs.orglett.2c00722

  日期：2022.3.18

  A mild method for the deborylation deuteration of arylboronic acids with D2O, mediated by the synergistic combination of a thiol, a Lewis base, and photoredox catalysis, is reported. This reaction showed a broad substrate scope, excellent deuterium incorporation, and functional group tolerance. Therefore, this method is practical for the site-selective D-labeling of bioactive molecules and drug molecules

  报道了一种由硫醇、路易斯碱和光氧化还原催化的协同组合介导的芳基硼酸与 D 2 O脱硼氘化的温和方法。该反应显示出广泛的底物范围、优异的氘掺入和官能团耐受性。因此，该方法对于生物活性分子和药物分子的位点选择性D标记是实用的。
• Synthesis of Non‐Terminal Alkenyl Ethers, Alkenyl Sulfides, and N‐Vinylazoles from Arylaldehydes or Diarylketones, DMSO and O, S, N‐Nucleophiles
  作者：Zhiwen Nie、Huifang Lv、Tonglin Yang、Miaodong Su、Weiping Luo、Qiang Liu、Cancheng Guo

  DOI：10.1002/adsc.202200020

  日期：2022.4.12

  A transition-metal-free protocol for the synthesis of non-terminal alkenyl ethers, alkenyl sulfides, and N-vinylazoles from arylaldehydes or diarylketones, DMSO and O, S, N-nucleophiles has been reported. In this protocol, 24 examples of non-terminal alkenyl ethers and 28 examples of non-terminal alkenyl sulfides in 72–95% yields have been synthesized within 5 min. Moreover, 27 examples of non-terminal

  已经报道了一种从芳醛或二芳基酮、DMSO 和 O、S、N-亲核试剂合成非末端烯基醚、烯基硫化物和 N-乙烯基唑的无过渡金属方案。在该协议中，在 5 分钟内合成了 24 个非末端烯基醚的例子和 28 个非末端烯基硫化物的例子，产率为 72-95%。此外，在 2 小时内还合成了 27 个非末端 N-乙烯基唑的例子，产率为 57-88%。初步机理研究表明，芳醛或二芳基酮提供了一个碳原子，DMSO提供了一个次甲基，O,S,N-亲核试剂贡献了一个X原子来构建C=C-X结构。
• RUSSELL, GLEN A.;YAO, CHING-FA;TASHTOUSH, HASAN I.;RUSSELL, JUNE E.;DEDOL+, J. ORG. CHEM., 56,(1991) N, C. 663-669
  作者：RUSSELL, GLEN A.、YAO, CHING-FA、TASHTOUSH, HASAN I.、RUSSELL, JUNE E.、DEDOL+

  DOI：——

  日期：——
• Addition, substitution and deoxygenation reactions of .alpha.-phenyl-.beta.-nitrostyrenes with the anions of thiols and diethyl phosphite: formation of indoles by reaction with ethyl phosphites
  作者：Glen A. Russell、Ching Fa Yao、Hasan I. Tashtoush、June E. Russell、Douglas F. Dedolph

  DOI：10.1021/jo00002a032

  日期：1991.1

  Reactions of excess RS- (R = Ph, t-Bu) with Ph2C = C(SPh)NO2 in Me2SO form Ph2C = CHSR via conversion of the initial Micheal-type adducts into Ph2C(SR)CH = NO2- and Ph2C = CHNO2. In a similar fashion, reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 forms initially mainly PhSP(O) (OEt)2 and PH2C[P(O)(OEt)2]CH = NO2-, which upon acidic workup will yield the nitroalkane or the Nef reaction product, Ph2C[P(O)(OEt)2]CHO. The reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 also produces Ph2C[P(O)(OEt)2] C = N via a perkow-type reaction of the Michael adduct to yield Ph2C[P(O)(OEt)2]CH = N(O)OP(O)(OEt)2 as an intermediate. The nitrile is also formed from Ph2C[P(O)(OEt)2]CH(NO2)2 with (EtO)2PO- in (EtO)2P(O)H or Me2SO at 30-degrees-C and in > 95% yield by the reaction of (EtO)3P with Ph2C[P(O)(OEt)2CH(NO2)2 at 150-degrees-C. Reaction of Ph2C = CHNO2 or Ph2C[P(O)(OEt)2]CH2NO2 with excess (EtO)2PO- in Me2SO or (EtO)2P(O)H forms 3-(diethoxyphosphinyl)-2,2-diphenylaziridine by a process postulated to involve Ph2C = CHN(O-)OP(O)(OEt)2, Ph2C = CHNOP(O)(OEt)2-, and 2,2-diphenyl-2H-azirine. Similarly, Ph2C = C(SBu-t)NO2 and (EtO)2PO- give 3-(tert-butylthio)-2,2-diphenyl-2H-azirine in Me2SO or 2-(tert-butylthio)-3-phenylindole in (EtO)2P(O)H solution. Deoxygenation of Ph2C = C(X)NO2 to form the 2-X-3-phenylindoles occurs in high yield at 150-degrees-C in (EtO)3P with X = H, PhS, or t-BuS while 2-nitro-3-phenylindole is formed from Ph2C = C(NO2)2 in (EtO)2P(O)H at 150-degrees-C.