3-phenyl-2-(phenylthio)indole | 131589-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-phenyl-2-(phenylthio)indole
• 英文别名: 3-phenyl-2-phenylsulfanyl-1H-indole
• CAS: 131589-85-0
• 化学式: C₂₀H₁₅NS
• 分子量: 301.412
• InChiKey: BMXYLWAUCNHHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-2-diazo-but-3-enoic acid ethyl ester 、 3-phenyl-2-(phenylthio)indole 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-chloro-4-(3-phenyl-2-phenylsulfanyl-3H-indol-3-yl)-but-2-enoic acid ethyl ester 、 4-chloro-4-(3-phenyl-2-phenylsulfanyl-3H-indol-3-yl)-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  高度非对映选择性的叶立德重排成季取代的二氢吲哚。

  摘要：

  DOI：

  10.1002/anie.200801336
• 作为产物：
  描述：

  1-nitro-1-(phenylthio)-2,2-diphenylethylene 在 亚磷酸三乙酯 作用下， 反应 0.5h， 以99%的产率得到3-phenyl-2-(phenylthio)indole
  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

• 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：——
• Highly Diastereoselective Sulfonium Ylide Rearrangements to Quaternary Substituted Indolines
  作者：Vyacheslav Boyarskikh、Abijah Nyong、Jon D. Rainier

  DOI：10.1002/anie.200801336

  日期：2008.7.7
• 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.