cis-3,4-dicarboxythiacyclopentane anhydride | 16810-52-9

• 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: cis-3,4-dicarboxythiacyclopentane anhydride
• 英文别名: cis-Thiophan-3,4-dicarbonsaeure-anhydrid；cis-tetrahydro-thiophene-3,4-dicarboxylic acid anhydride；(3ar,6ac)-tetrahydro-thieno[3,4-c]furan-1,3-dione；cis-Tetrahydro-thiophen-3,4-dicarbonsaeure-anhydrid；(3aS,6aR)-3a,4,6,6a-tetrahydrothieno[3,4-c]furan-1,3-dione
• CAS: 16810-52-9
• 化学式: C₆H₆O₃S
• 分子量: 158.178
• InChiKey: QPUHIMKBVJKERM-ZXZARUISSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  145-148 °C(Press: 1 Torr)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-3,4-dicarboxythiacyclopentane anhydride 在 lithium aluminium tetrahydride 、 乙醚 、 硫酸 、 水 、 silver(l) oxide 作用下， 生成 1,3,4-三甲基吡咯
  参考文献：
  名称：

  Further Attempts to Prepare 3,4-Dimethylenethiophane and its Sulfone¹

  摘要：

  DOI：

  10.1021/ja01604a060
• 作为产物：
  描述：

  2,5-dihydrothiophene-3,4-dicarboxylic acid 在 乙酰氯 作用下， 生成 cis-3,4-dicarboxythiacyclopentane anhydride
  参考文献：
  名称：

  生物素 3，4-反式-二氨基噻吩。

  摘要：

  DOI：

  10.1021/jo01165a019

文献信息

• Enzymes in organic synthesis-29
  作者：George S.Y. Ng、Lung-Chi Yuan、Ignac J. Jakovac、J. Bryan Jones

  DOI：10.1016/s0040-4020(01)82410-8

  日期：——

  alcohol dehydrogenase-catalyzed oxidations of meso-diols as a route to chiral lactones of asymmetric synthetic value are described. The acyclic meso substrates, cis-2,3-dimethyl- and -diethylbutane-l,4-diols, and cis-2,4-dimethylpentane-l,5diol, are stereospecifically oxidized in good yields to the corresponding enantiomerically pure γ- and δ-lactones. The oxidation of cis-3,4-bis(hydroxymethyl)thiacyclopentane

  描述了马肝醇脱氢酶催化的内消旋二醇的氧化作为制备不对称合成值的手性内酯的途径的广泛应用的其他实例。无环内消旋底物顺式-2,3-二甲基-和-二乙基丁烷-1,4-二醇和顺式-2,4-二甲基戊烷-1,5-二醇以良好的产率被立体定向​​氧化为相应的对映体纯的γ-和δ-内酯。顺式-3,4-双（羟甲基）硫代环戊烷的氧化类似地是立体定向的。对于每个中观-二醇的氧化反应对连接到S-enter上的羟甲基基团具有净立体定向性，最初形成的羟醛通过其半缩醛形式进行进一步的酶催化氧化，从而直接生成内酯产物。
• The Preparation of<i>cis</i>-3,4-Ureylenethiophane
  作者：Takao Takaya、Hataaki Yoshimoto、Eiji Imoto

  DOI：10.1246/bcsj.40.2636

  日期：1967.11

  The preparation of cis-3,4-ureylenethiophane (23) was attempted through three different routes. cis-3-Carbomethoxyamino-4-carbomethoxythiophane (20A), which had been obtained by the Lossen rearrangement of N-phenylsulfonyloxythiophane-cis-3, 4-dicarboximide (19), was selectively hydrolyzed to cis-3-carbomethoxyamino-4-carboxythiophane (21A), the modified Curtius rearrangement of which gave N-carbomethoxy-cis-3

  通过三种不同的途径尝试制备顺式 3,4-亚脲基噻吩 (23)。通过 N-苯基磺酰氧基噻吩-顺-3, 4-二甲酰亚胺 (19) 的洛森重排获得的顺式-3-甲氧基氨基-4-甲氧基噻吩 (20A) 被选择性水解为顺式-3-甲氧基氨基-4-羧基噻吩(21A)，其改良的 Curtius 重排得到 N-碳甲氧基-顺-3, 4-亚脲基噻吩 (22A)。22A 的碱性水解得到 23。然而，试图通过两种砜衍生物 (6) 和 (14) 制备 23 没有成功。
• Novel antifungal β-amino acids: synthesis and activity against Candida albicans
  作者：Joachim Mittendorf、Franz Kunisch、Michael Matzke、Hans-Christian Militzer、Axel Schmidt、Wolfgang Schönfeld

  DOI：10.1016/s0960-894x(02)00958-7

  日期：2003.2

  A series of novel beta-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. beta-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
  作者：Ali Thaqi、Janet L. Scott、Jayne Gilbert、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.ejmech.2010.01.004

  日期：2010.5

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.
• An Attempted Synthesis of 3,4-Dimethylenethiophane¹
  作者：C. S. Marvel、E. E. Ryder

  DOI：10.1021/ja01606a019

  日期：1955.1