tert-butyl (2S)-2-vinylindolinecarboxylate | 313235-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl (2S)-2-vinylindolinecarboxylate
• 英文别名: tert-butyl (S)-2-vinylindoline-1-carboxylate；(2S)-1-tert-butoxycarbonyl-2-vinylindoline；tert-butyl (2S)-2-ethenyl-2,3-dihydroindole-1-carboxylate
• CAS: 313235-16-4
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: ITZOEVNFHYTNKQ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-vinylindolinecarboxylate 在 TEA 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 35.0h， 生成 1-((2S)-2-vinylindolinyl)-2-{4-[(4-chlorophenyl)methyl]piperazinyl}ethan-1-one
  参考文献：
  名称：

  Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation

  摘要：

  A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D-2 and D-4 receptors. Three compounds having D-2/D-4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00656-x
• 作为产物：
  描述：

  1-tert-butoxycarbonyl-2-indolinecarboxaldehyde 在 正丁基锂 、 甲基三苯基溴化膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到tert-butyl (2S)-2-vinylindolinecarboxylate
  参考文献：
  名称：

  Benzylpiperazinyl-indolinylethanones

  摘要：

  公开了苯甲基哌嗪基-吲哚啉基乙酮化合物，这些化合物对于治疗和/或预防包括但不限于精神分裂症、躁狂症、痴呆、抑郁症、焦虑症、强迫行为、物质滥用、类似帕金森病的运动障碍以及与使用神经安定药物相关的运动障碍等神经心理障碍具有用途。此外，还提供了包括包装药品在内的药物组合物。本发明的化合物还可作为探针用于组织样本中GABAA受体的定位。

  公开号：

  US06355644B1

文献信息

• Enantioselective Synthesis of Pyrrolidine-, Piperidine-, and Azepane-Type <i>N</i>-Heterocycles with α-Alkenyl Substitution: The CpRu-Catalyzed Dehydrative Intramolecular <i>N</i>-Allylation Approach
  作者：Tomoaki Seki、Shinji Tanaka、Masato Kitamura

  DOI：10.1021/ol203218d

  日期：2012.1.20

  acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH2CH═CH2] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz

  阳离子CPRU复杂的手性吡啶甲酸衍生物[（的[R ）-或（小号）-Cl-的Naph-PyCOOCH 2 CH = CH 2 ]催化不对称分子内脱水Ñ的-allylation Ñ取代ω氨基-和氨基羰基烯丙基醇底物/催化剂比例最高为2000，可得到对映体比例最高> 99：1的α-烯基吡咯烷-，哌啶-和氮杂环庚烷型N-杂环。广泛适用的N取代基，包括Boc，Cbz，Ac，Bz，丙烯酰基，巴豆酰基，甲酰基和Ts，极大地促进了对天然产物合成的进一步控制。
• Hg(OTf)2-BINAPHANE-Catalyzed Enantioselective Anilino Sulfonamide Allyl Alcohol Cyclization
  作者：Hirofumi Yamamoto、Elisabeth Ho、Kosuke Namba、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1002/chem.201001656

  日期：——

  Chiral ligands: Hg(OTf)2‐catalyzed cyclization of anilino sulfonamide allyl alcohol is described; this reaction gives 2‐vinyl indoline derivatives in good yields and excellent enantioselectivity by using a chiral BINAPHANE ligand (see scheme).

  手性配体：Hg（OTf）2催化苯胺磺酰胺烯丙醇的环化反应；通过使用手性BINAPHANE配体，该反应可得到高收率和出色的对映选择性的2-乙烯基二氢吲哚衍生物（参见方案）。
• Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp ³ )−H Bond Amination Upon Visible‐Light Irradiation
  作者：Hua‐Hua Wang、Hui Shao、Guanglong Huang、Jianqiang Fan、Wai‐Pong To、Li Dang、Yungen Liu、Chi‐Ming Che

  DOI：10.1002/anie.202218577

  日期：——

  An efficient method has been developed for the chiral iron porphyrin catalyzed transformation of aryl and arylsulfonyl azides into chiral indolines and sultams, respectively. The reaction proceeds upon visible light irradiation and with high yields and excellent enantioselectivities.

  开发了一种有效的方法，用于手性铁卟啉催化芳基叠氮化物和芳基磺酰叠氮化物分别转化为手性二氢吲哚和磺胺类化合物。该反应在可见光照射下进行，产率高，对映体选择性好。
• Benzylpiperazinyl-indolinylethanones
  申请人：Neurogen Corporation

  公开号：US06355644B1

  公开（公告）日：2002-03-12

  Disclosed are benzylpiperazinyl-indolinylethanone compounds which are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents. Pharmaceutical compositions, including packaged pharmaceutical compositions, are further provided. Compounds of the invention are also useful as probes for the localization of GABAA receptors in tissue samples.

  公开了苯甲基哌嗪基-吲哚啉基乙酮化合物，这些化合物对于治疗和/或预防包括但不限于精神分裂症、躁狂症、痴呆、抑郁症、焦虑症、强迫行为、物质滥用、类似帕金森病的运动障碍以及与使用神经安定药物相关的运动障碍等神经心理障碍具有用途。此外，还提供了包括包装药品在内的药物组合物。本发明的化合物还可作为探针用于组织样本中GABAA受体的定位。
• Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation
  作者：He Zhao、Xiaoshu He、Andrew Thurkauf、Diane Hoffman、Andrzej Kieltyka、Robbin Brodbeck、Renee Primus、Jan W.F Wasley

  DOI：10.1016/s0960-894x(02)00656-x

  日期：2002.11

  A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D-2 and D-4 receptors. Three compounds having D-2/D-4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects. (C) 2002 Elsevier Science Ltd. All rights reserved.