1,2-diacetoxy-1,2,3,4-tetrahydro-naphthalene | 16814-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2-diacetoxy-1,2,3,4-tetrahydro-naphthalene
• 英文别名: (1S)-trans-1,2-diacetoxy-1,2,3,4-tetrahydro-naphthalene；(1S)-trans-1,2-Diacetoxy-1,2,3,4-tetrahydro-naphthalin；trans-Tetralin-1,2-diol, diacetate；[(1S,2S)-1-acetyloxy-1,2,3,4-tetrahydronaphthalen-2-yl] acetate
• CAS: 16814-46-3；16821-30-0；88230-00-6；88230-02-8
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: PWDTYDXUIYVSGG-KBPBESRZSA-N

物化性质

• 熔点：
  78.6-79.4 °C
• 沸点：
  340.5±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 保留指数：
  1705

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-diacetoxy-1,2,3,4-tetrahydro-naphthalene 在 水 作用下， 生成 1,2-Naphthalenediol, 1,2,3,4-tetrahydro-, 2-acetate 、 1,2-Naphthalenediol, 1,2,3,4-tetrahydro-, 2-acetate
  参考文献：
  名称：

  Enantioselective ester hydrolyses employing Rhizopus nigricans. A method of preparing and assigning the absolute stereochemistry of cyclic alcohols

  摘要：

  DOI：

  10.1021/jo00178a020
• 作为产物：
  描述：

  2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol 在 氢溴酸 、 溶剂黄146 、 苯 作用下， 生成 1,2-diacetoxy-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  Straus; Rohrbacher, Chemische Berichte, 1921, vol. 54, p. 57

  摘要：

  DOI：

文献信息

• B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant
  作者：Jiuzhong Huang、Lu Ouyang、Jianxiao Li、Jia Zheng、Wuxin Yan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.8b01806

  日期：2018.9.7

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
• Palladium-Catalyzed Olefin Dioxygenation
  作者：Yang Li、Datong Song、Vy M. Dong

  DOI：10.1021/ja711029u

  日期：2008.3.1

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.
• Criegee, Justus Liebigs Annalen der Chemie, 1930, vol. 481, p. 263,286
  作者：Criegee

  DOI：——

  日期：——
• Metal-Free, Organocatalytic <i>Syn</i> Diacetoxylation of Alkenes
  作者：Wenhe Zhong、Shan Liu、Jun Yang、Xiangbao Meng、Zhongjun Li

  DOI：10.1021/ol301311e

  日期：2012.7.6

  A novel method for the organocatalytic syn diacetoxylation of alkenes has been developed using aryl iodides as efficient catalysts. A broad range of substrates, including electron-rich as well as electron-deficient alkenes, are smoothly transformed by the new procedure, furnishing the desired products in good to excellent yields with high diastereoselectivity (up to >19:1 dr).
• Ruthenium- and lipase-catalyzed DYKAT of 1,2-diols: an enantioselective synthesis of syn-1,2-diacetates
  作者：Michaela Edin、Belén Martín-Matute、Jan-E. Bäckvall

  DOI：10.1016/j.tetasy.2006.02.011

  日期：2006.2

  Regio- and stercoselective lipase-catalyzed kinetic resolutions were investigated for some unsymmetrical, secondary/secondary syn-diols. Candida antarctica lipase B-catalyzed transesterifications of a few aryl/alkyl- and alkyl/alkyl 1,2-diols were coupled in one-pot for efficient ruthenium-catalyzed epimerization and intramolecular acyl migration to give a dynamic kinetic asymmetric transformation (DYKAT) affording enantioenriched (ee up to > 99%) syn-diacetates as the main diastereomers (sywanti similar to 2:1 to 10:1). (c) 2006 Elsevier Ltd. All rights reserved.