(1S,2R)-2-acetoxy-1-hydroxyindane | 220886-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2R)-2-acetoxy-1-hydroxyindane
• 英文别名: (1S,2R)-2-acetoxy-1-indanol；(1S,2R)-2-acetoxyindan-1-ol；[(1S,2R)-1-hydroxy-2,3-dihydro-1H-inden-2-yl] acetate
• CAS: 220886-51-1
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: HQFWBMOCEGVZBV-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-acetoxy-1-hydroxyindane 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 (1S,2R)-(-)-1-氨基-2-茚醇
  参考文献：
  名称：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol and the Ritter reaction of its mono-acetate

  摘要：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol 5 in the presence of lipase PS was examined. Enantiomerically enriched (1S,2R)-2-acetoxy-1-indanol 6a was obtained when cis-1,2-indandiol 5 was treated with one equivalent of vinyl acetate. Treatment of 5 with two equivalents of vinyl acetate furnished a mixture of (1R,2S)-2-acetoxy-1-indanol 6a and (1R,2S)-1-acetoxy-2-indanol 6b. A route to both enantiomers of a was also developed by using the enantiomerically enriched mono-acetate thus obtained. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00006-4
• 作为产物：
  描述：

  trans-2-bromo-1-indanol 、 乙酸酐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 以74%的产率得到(1S,2R)-2-acetoxy-1-hydroxyindane
  参考文献：
  名称：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol and the Ritter reaction of its mono-acetate

  摘要：

  Lipase-mediated kinetic resolution of cis-1,2-indandiol 5 in the presence of lipase PS was examined. Enantiomerically enriched (1S,2R)-2-acetoxy-1-indanol 6a was obtained when cis-1,2-indandiol 5 was treated with one equivalent of vinyl acetate. Treatment of 5 with two equivalents of vinyl acetate furnished a mixture of (1R,2S)-2-acetoxy-1-indanol 6a and (1R,2S)-1-acetoxy-2-indanol 6b. A route to both enantiomers of a was also developed by using the enantiomerically enriched mono-acetate thus obtained. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00006-4

文献信息

• Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins
  作者：He Huang、Tristan H. Lambert

  DOI：10.1021/jacs.1c01967

  日期：2021.5.19

  conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

  描述了在电光催化条件下具有顺式立体选择性的烯烃乙酰氧基羟基化的方法。该过程使用三氨基环丙烯 (TAC) 离子催化剂，在受控电化学势下进行可见光照射，将芳基烯烃转化为具有高化学和非对映选择性的相应乙二醇单酯。该反应可以分批或流动进行，从而能够合成多克单酯产物。
• Enantioselective Prévost and Woodward reactions using chiral hypervalent iodine(iii): switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation
  作者：Morifumi Fujita、Mikimasa Wakita、Takashi Sugimura

  DOI：10.1039/c1cc10129c

  日期：——

  Optically active 1,3-dioxolan-2-yl cation intermediates were generated during enantioselective dioxyacetylation of alkene with chiral hypervalent iodine(III). Regioselective attack of a nucleophile toward the intermediate resulted in reversal of enantioselectivity of the dioxyacetylation.

  用手性高价碘（III）对烯烃进行对映选择性二氧乙酰化时，生成了旋光的1,3-二氧杂戊-2-基阳离子中间体。亲核试剂对中间体的区域选择性攻击导致二氧乙酰化的对映选择性逆转。
• Scandium Trifluoromethanesulfonate-Catalyzed Cleavage of Esters Bearing a Coordinative Group at a Vicinal Position
  作者：Hiroshi Kajiro、Shuichi Mitamura、Atsunori Mori、Tamejiro Hiyama

  DOI：10.1246/bcsj.72.1553

  日期：1999.7

  Scandium trifluoromethanesulfonate is found to be a Lewis acid catalyst for selective cleavage of esters containing a coordinative group adjacent to an ester moiety. The reaction proceeds under weak acidic conditions at room temperature; the catalyst can be recovered and reused. Even α-acyloxy ketones are deacetylated without racemization. Selective monodeacetylation at C-10 of paclitaxel has been achieved.

  研究发现，三氟甲磺酸钪是一种路易斯酸催化剂，可选择性地裂解含有邻近酯分子的配位基团的酯。反应在室温下的弱酸性条件下进行；催化剂可以回收和重复使用。即使是 α-乙酰氧基酮也能脱乙酰化而不发生外消旋化。在紫杉醇的 C-10 处实现了选择性单去乙酰化。
• The Role of Neighboring Groups in Replacement Reactions. XX. Some Conversions of Cyclopentane and Indan Derivatives¹
  作者：S. Winstein、Royston M. Roberts

  DOI：10.1021/ja01106a003

  日期：1953.5
• JPH1135533A
  申请人：——

  公开号：JPH1135533A

  公开（公告）日：1999-02-09