(R)-tert-butyl 2,5-dichloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate | 1224373-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-tert-butyl 2,5-dichloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: tert-butyl (R)-2,5-dichloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate；(-)-2,5-dichloro-1-oxoindan-2-carboxylic acid tert-butyl ester；(+)-2,5-dichloro-1-oxoindan-2-carboxylic acid tert-butyl ester
• CAS: 1224373-78-7
• 化学式: C₁₄H₁₄Cl₂O₃
• 分子量: 301.169
• InChiKey: KFPCODFPORAOIC-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  tert-butyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 在 C₇₂H₄₉F₂₄NO₆P₂ 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以99%的产率得到(R)-tert-butyl 2,5-dichloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  对映选择性α的-chlorination β酮酯和酰胺催化通过手性酸imidodiphosphoric

  摘要：

  手性酸imidodiphosphoric被雇用作为催化剂用于对映选择性α的-chlorination β酮酯和使用NCS作为氯源，提供一系列的光学活性产物具有良好的高对映选择性（74-95％ee）和优良产率的酰胺（ 92–99％）。这代表了布朗斯台德酸催化的环状β-酮衍生物对映选择性α-氯化反应的首次报道。

  DOI：

  10.1016/j.tetlet.2018.05.024

文献信息

• Cu(I)-catalyzed asymmetric chlorination of β-keto esters in the presence of chiral phosphine-schiff base type ligands
  作者：Jia-Jun Jiang、Jian Huang、De Wang、Zhi-Liang Yuan、Mei-Xin Zhao、Fei-Jun Wang、Min Shi

  DOI：10.1002/chir.20913

  日期：2011.3

  Chiral phosphine‐Schiff base type ligand L8 prepared from (R)‐(−)‐2‐(diphenylphosphino)‐1,1'‐binaphthyl‐2'‐amine was found to be a fairly effective ligand for Cu(I)‐promoted enantioselective chlorination of β‐keto esters to give the corresponding products in high yields and with moderate enantioselectivities. Chirality 2011. © 2010 Wiley‐Liss, Inc.

  由（R）-（-）-2-（二苯基膦基）-1,1'-联萘-2-'胺制备的手性膦Schiff碱型配体L8被发现是Cu（I）促进的相当有效的配体β-酮酯的对映选择性氯化，以高收率和中等对映选择性得到相应的产物。手性2011。©2010 Wiley-Liss，Inc.。
• Asymmetric α‐Chlorination of β‐Keto Esters Using Hypervalent Iodine‐Based Cl‐Transfer Reagents in Combination with Cinchona Alkaloid Catalysts
  作者：Lotte Stockhammer、Johannes Schörgenhumer、Christopher Mairhofer、Mario Waser

  DOI：10.1002/ejoc.202001217

  日期：2021.1.8

  Simple Cinchona alkaloids serve as nucleophilic organocatalysts to facilitate the enantioselective α‐chlorination of β‐keto esters by using hypervalent iodine‐based Cl‐transfer reagents

  简单的金鸡纳生物碱作为亲核有机催化剂，通过使用高价碘基 Cl 转移试剂促进 β-酮酯的对映选择性 α-氯化
• Asymmetric Chlorination of Cyclic β-Keto Esters and N-Boc Oxindoles­ Catalyzed by an Iron(III)-BPsalan Complex
  作者：Zhen-Jiang Xu、Chi-Ming Che、Yong-Heng Luo、Yuan-Ji Ping、Zong-Rui Li、Xin Gu

  DOI：10.1055/s-0036-1590955

  日期：2018.3

  Abstract An iron(III)-BPsalan complex was found to efficiently catalyze the asymmetric chlorination reaction of cyclic β-keto esters and N-Boc oxindoles, affording the corresponding chlorinated products in high yield and up to 92% ee with NCS as chlorination reagent under mild reaction conditions. An iron(III)-BPsalan complex was found to efficiently catalyze the asymmetric chlorination reaction of

  摘要 发现铁（III）-BPsalan络合物可有效催化环状β-酮酯和N - Boc羟吲哚的不对称氯化反应，在温和的条件下以NCS作为氯化试剂，可提供高产率和高达92％ee的相应氯化产物。反应条件。 发现铁（III）-BPsalan络合物可有效催化环状β-酮酯和N - Boc羟吲哚的不对称氯化反应，在温和的条件下以NCS作为氯化试剂，可提供高产率和高达92％ee的相应氯化产物。反应条件。
• Enantioselective direct fluorination and chlorination of cyclic β-ketoesters mediated by phase-transfer catalysts
  作者：Jie Luo、Wenqin Wu、Li-Wen Xu、Yuezhong Meng、Yixin Lu

  DOI：10.1016/j.tetlet.2013.03.028

  日期：2013.5

  A straightforward and practical method for the direct fluorination and chlorination of various beta-ketoesters employing a phase-transfer catalyst is developed. The desired products with fluorine/chlorine-substituted quaternary chiral centers are prepared with good to excellent enantioselectivities. (c) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric α-chlorination of β-ketoesters using bifunctional ammonium salt catalysis
  作者：Johanna Novacek、Uwe Monkowius、Markus Himmelsbach、Mario Waser

  DOI：10.1007/s00706-015-1604-7

  日期：2016.3

  Chiral urea-quaternary ammonium salt hybrid organocatalysts were tested for their capability to control asymmetric alpha-chlorination reactions of beta-ketoesters. After a careful screening we identified a structurally simple catalyst derivative that allowed us to obtain enantiomeric ratios up to 90:10 under operationally simple conditions using just 1 mol% of the catalyst.[GRAPHICS].