N-phthalimide l-methioninyl chloride | 74198-48-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phthalimide l-methioninyl chloride
• 英文别名: phthaloyl-Met-Cl；(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylsulfanylbutanoyl chloride
• CAS: 74198-48-4
• 化学式: C₁₃H₁₂ClNO₃S
• 分子量: 297.762
• InChiKey: XKWBIBFHTFFEIJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-phthalimide l-methioninyl chloride 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

  摘要：

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。

  DOI：

  10.1055/s-0034-1380384
• 作为产物：
  描述：

  苯酐 在 氯化亚砜 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 N-phthalimide l-methioninyl chloride
  参考文献：
  名称：

  Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

  摘要：

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。

  DOI：

  10.1055/s-0034-1380384

文献信息

• Primary, Secondary, and Tertiary γ-C(sp³)–H Vinylation of Amides via Organic Photoredox-Catalyzed Hydrogen Atom Transfer
  作者：Hui Chen、Liangliang Guo、Shouyun Yu

  DOI：10.1021/acs.orglett.8b02737

  日期：2018.10.5

  An efficient strategy for primary, secondary and tertiary aliphatic γ-C(sp3)–H vinylation of amides with alkenylboronic acids is reported. These reactions are catalyzed by visible-light organic photoredox agents. Regioselective γ-C(sp3)–H vinylation of amides is controlled by a 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

  据报道，用烯基硼酸对酰胺的伯，仲和叔脂族γ-C（sp 3）-H进行乙烯基化的有效策略。这些反应由可见光有机光氧化还原剂催化。酰胺的区域选择性γ-C（sp 3）–H乙烯基化是由就地生成的mid基的1，5-氢原子转移控制的。
• Synthesis and properties of photoacylotropic (2Z)-2-(N-acyl-N-arylaminomethylidene)benzo[b]thiophen-3(2H)-ones with a chiral migrating group
  作者：V. P. Rybalkin、Ya. Yu. Vorob’eva、G. S. Borodkin、A. D. Dubonosov、A. V. Tsukanov、V. V. Tkachev、S. M. Aldoshin、V. A. Bren’、V. I. Minkin

  DOI：10.1007/s11172-006-0191-5

  日期：2005.12

  New photochromic (2Z)-2-(N-acyl-N-arylaminomethylidene)benzo[b]thiophen-3(2H)-ones containing L-amino acid derivatives as migrating groups were synthesized. Light irradiation of their solutions at 436 nm leads to the photoinduced acylotropic rearrangement N → O accompanied by migration of the chiral fragment. The bulky N-acyl group causes steric strain thus destabilizing the amide form of compounds

  合成了含有 L-氨基酸衍生物作为迁移基团的新型光致变色 (2Z)-2-(N-酰基-N-芳基氨基亚甲基)苯并 [b] 噻吩-3(2H)-one。他们的溶液在 436 nm 的光照射导致光诱导的非变性重排 N → O 伴随着手性片段的迁移。庞大的 N-酰基会导致空间应变，从而使化合物的酰胺形式不稳定并促进光重排。
• Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols
  作者：Yujiro Hoshino、Hisashi Yamamoto

  DOI：10.1021/ja002602o

  日期：2000.10.1
• Chiron based synthesis of isocoumarins: reactivity of α-substituted carboxylic acids
  作者：Aisha Saddiqa、Abdul R. Raza、David StC. Black、Naresh Kumar

  DOI：10.1016/j.tetasy.2014.03.019

  日期：2014.5

  The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and alpha-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with alpha-chloro-acids afforded asymmetric isocoumarins in high yield. (C) 2014 Elsevier Ltd. All rights reserved.
• 1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
  作者：Zhiwei Miao、Haihong Ge、Shuang Liu、Yan Cai、Yuchao Sun

  DOI：10.1055/s-0035-1560373

  日期：——

  The regiospecific and stereoselective 1,2-migration reaction of dialkyl alpha-diazophosphonates for the synthesis of beta-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)(4)PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to beta-amino (E)-enylphosphonates in moderate to good yields.