rel-(1R,2S)-cyclopentane-1,2-diol diacetate | 37854-32-3

• 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: rel-(1R,2S)-cyclopentane-1,2-diol diacetate
• 英文别名: cis-cyclopentane-1,2-diyl diacetate；cis-1,2-cyclopentanediol diacetate；meso-1,2-diacetoxycyclopentane；cis-1,2-diacetoxycyclopentane；cis-1.2-diacetoxy-cyclopentane；cis-1.2-Diacetoxy-cyclopentan；[(1S,2R)-2-acetyloxycyclopentyl] acetate
• CAS: 37854-32-3；26620-22-4；35657-88-6；65783-98-4；105663-23-8；110611-65-9；133442-59-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: BXAYTJKZGSJCRS-DTORHVGOSA-N

物化性质

• 熔点：
  -5.0 °C
• 沸点：
  80-80.5 °C(Press: 2 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  rel-(1R,2S)-cyclopentane-1,2-diol diacetate 在 草酰氯 、 Amano PS Lipase 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 、 Petroleum ether 、 苯 为溶剂， 反应 18.25h， 生成 2-acetoxycyclopentanone
  参考文献：
  名称：

  Enantioselective enzymatic approach to (+)- and (−)-2-acetoxy/hydroxycyclopentanones

  摘要：

  A new practical enzymatic approach to (+)- and (-)-2-acetoxy/hydroxycyclopentanones with 96-98% ee has been described via enzymatic hydrolysis of the meso-diacetate 2, Swern oxidation of the thus formed (+/-)-hydroxy acetates 3 and 4, followed by re-enzymatic resolution. Enantiomerically pure (+)- and (-)-2-hydroxycyclopentanones are in equilibrium with enediol 9 and slowly undergo racemisation, a process which could be arrested by protecting the hydroxyl group as the acetate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00366-x
• 作为产物：
  描述：

  (1R,2S)-(-)-1-acetoxy-2-hydroxycyclopentane 生成 rel-(1R,2S)-cyclopentane-1,2-diol diacetate
  参考文献：
  名称：

  GREWAL G. S., J. RES. PUNJAB AGR. UNIV., 1977, 14, NO 4, 468-472

  摘要：

  DOI：

文献信息

• Synthesis of an Isotopically Isomeric Mixture of 1,4,6,8-Tetramethyl[13C2]azulene and Its Thermal Reaction with Dimethyl Acetylenedicarboxylate
  作者：Reza-Ali Fallahpour、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19950780604

  日期：1995.9.20

  8-tetramethyl[1,3-13C2]-, -[1,3a-13C2]-, -[2,3a-13C2]-, -[2,8a-13C2]-, and -[3,8a-13C2]azulene (5; cf. Scheme 8 and Fig. 2). The measured 2J(13C, 13C) values of [13C2]-20 and [13C2]-5 are listed in Tables 1 and 2. Thermal reaction of the 1:1:1:1:1 mixture [13C2]-5 with the four-fold amount of dimethyl acetylenedicarboxylate (ADM) at 200° in tetralin (cf. Scheme 2) gave 5,6,8,10-tetramethyl-[13C2]heptalene-1

  由相应的标记的[ 13 C 2 ]环戊二烯制备四氢呋喃（THF）中的[1,3- 13 C 2 ]环戊二烯酸钠，由相应的标记物由13 CO 2和（氯甲基）三甲基硅烷合成（参见方案10），根据既定程序。它可以表明的乙酸热解顺式-环戊烷-1,2-二基二乙酸酯（顺式- 22）在550±5°下减压（60托），得到5倍的环戊二烯如反式- 22。钠[1,3- 13 C 2]环戊二烯与THF中的2,4,6-三甲基四氟硼酸吡啶鎓导致形成统计上预期的4,6,8-三甲基[1,3a- 13 C 2 ]，-[2,3a] 2：2：1混合物- 13 ç 2 ] - ，以及- [1,3- 13 ç 2 ]薁（20 ;参见方案7和图1）。2：2：1混合物[ 13 C 2 ] -20的甲酰化和还原导致形成1,4,6,8-四甲基[1,3- 13 ]的1：1：1：1：1混合物C 2 ]-，-[1,3a- 13 C 2 ]-，-[2
• Dihydroxylation of olefins catalyzed by zeolite-confined osmium(0) nanoclusters: an efficient and reusable method for the preparation of 1,2-cis-diols
  作者：Önder Metin、Nurdan Alcan Alp、Serdar Akbayrak、Abdullah Biçer、Mehmet Serdar Gültekin、Saim Özkar、Uğur Bozkaya

  DOI：10.1039/c2gc16616j

  日期：——

  developed for the dihydroxylation of various olefins yielding 1,2-cis-diols. In our protocol, zeolite-confined osmium(0) nanoclusters (zeolite-Os0) are used as reusable catalyst and H2O2 served as a co-oxidant. Zeolite-Os0 are found to be highly efficient and selective catalysts for the dihydroxylation of a wide range olefins in an aqueous acetone mixture at room temperature. In all of the olefins surveyed

  本文讨论的是一种新型的，生态友好的，可回收的，可重复使用的和可瓶装的催化体系，用于各种羟基化 烯烃产生1，2-顺式-二醇。在我们的协议中沸石-confined锇（0）纳米团簇（沸石-锇0）被用作可重复使用的催化剂H 2 O 2为助氧化剂。发现Zeolite-Os 0高效且具有选择性催化剂 用于广泛的二羟基化 烯烃在室温下在丙酮水溶液中的溶液中。在所有的烯烃据调查，催化二羟基化反应顺利进行，在优化的条件下以优异的化学收率获得了相应的1，2-顺式-二醇。本发明的多相催化剂体系具有许多优势，例如与传统的均相OsO 4 -NMO体系相比，具有生态友好性和工业适用性，可将二羟基化烯烃。
• Enantioselective hydrolysis of five-membered-ring acetates catalysed by Pseudomonas fluorescens lipase
  作者：Zhuo-Feng Xie、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1039/c39870000838

  日期：——

  The racemic acetates of five-membered-ring alcohols were successfully resolved into the optically active alcohols with high optical purities by Pseudomonas fluorescens lipase.

  五元环醇的外消旋乙酸酯已通过荧光假单胞菌脂肪酶成功拆分为具有高光学纯度的旋光醇。
• Adrenaline profiling of lipases and esterases with 1,2-diol and carbohydrate acetates
  作者：Denis Wahler、Olivier Boujard、Fabrice Lefèvre、Jean-Louis Reymond

  DOI：10.1016/j.tet.2003.11.059

  日期：2004.1

  The adrenaline test for enzymes is a general back-titration procedure to detect 1,2-diols, 1,2-aminoalcohols and alpha-hydroxyketones reaction products of enzyme catalysis by colorimetry. The method was used to profile a series of esterases and lipases for their esterolytic activity on a series of carbohydrate and polyol acetates. Substrates were prepared by peracetylation and used for parallel microtiter-plate analysis of enzyme activities. This method can be used to achieve a rapid and automated characterization of a set of enzymes during HTS screening. (C) 2003 Elsevier Ltd. All rights reserved.
• Reduktinsäure, ein stark reduzierendes Abbauprodukt aus Kohlehydraten. II. Mitteilung
  作者：T. Reichstein、R. Oppenauer

  DOI：10.1002/hlca.19340170145

  日期：——