(3aS,6aR)-2,2-二甲基-4,6a-二氢-3aH-环戊二烯并[d][1,3]二氧杂环戊烯-4-醇 | 683276-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3aS,6aR)-2,2-二甲基-4,6a-二氢-3aH-环戊二烯并[d][1,3]二氧杂环戊烯-4-醇
• 英文名称: (4R,5S)-4,5-O-isopropylidenecyclopenten-1-ol
• 英文别名: (3aS,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 683276-44-0
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FXOFSGSXPYHEMV-FWPZAIACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,6aR)-2,2-二甲基-4,6a-二氢-3aH-环戊二烯并[d][1,3]二氧杂环戊烯-4-醇 在 六甲基磷酰三胺 、 三甲基氯硅烷 、 copper(I) bromide dimethylsulfide complex 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3aR,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one
  参考文献：
  名称：

  Yang, Minmin; Ye, Wei; Schneller, Stewart W., Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3993 - 3996

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 Grubbs catalyst first generation 、 sodium periodate 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 41.67h， 生成 (3aS,6aR)-2,2-二甲基-4,6a-二氢-3aH-环戊二烯并[d][1,3]二氧杂环戊烯-4-醇
  参考文献：
  名称：

  仿生异戊烯A和Sterhirsutins A和B的核心骨架的一般仿生杂Diels-Alder方法

  摘要：

  描述了对异戊烯烯A的5,6,11-三环核心骨架，以及甾体素A和B的仿生，区域和立体选择性方法。关键步骤是仿生反电子需求的α-hu草烯和核糖衍生的乙烯基酮的异Diels-Alder环加成电子，然后进行酸催化的1,3-二氧戊环重排，使其与生成的环状烯醇醚相邻。

  DOI：

  10.1021/acs.orglett.8b04003

文献信息

• USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS
  申请人：Peyrot Des Gachons Catherine

  公开号：US20110020424A1

  公开（公告）日：2011-01-27

  The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

  这项发明提供了油酸甘露醇类似物以及在各种配方中使用油酸甘露醇的方法，包括食品添加剂；药品；化妆品；动物驱避剂；以及用于哺乳动物刺激受体基因、基因产物、等位基因、剪接变体、替代转录本等的发现工具。
• [EN] COMPOUNDS TARGETING PRMT5<br/>[FR] COMPOSÉS CIBLANT PRMT5
  申请人：ALIGOS THERAPEUTICS INC

  公开号：WO2020205867A1

  公开（公告）日：2020-10-08

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

  本文提供了式（I）的化合物或其药用盐，包括含有本文描述的化合物（包括本文描述的化合物的药用盐）的药物组合物以及合成这些化合物的方法。本文还提供了使用式（I）的化合物或其药用盐治疗疾病和/或症状的方法。
• Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1021/jo702635t

  日期：2008.4.1

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.
• Identification of a cytotoxic molecule in heat-modified citrus pectin
  作者：Lionel Leclere、Maude Fransolet、Pierre Cambier、Sandy El Bkassiny、Abdellatif Tikad、Marc Dieu、Stéphane P. Vincent、Pierre Van Cutsem、Carine Michiels

  DOI：10.1016/j.carbpol.2015.10.055

  日期：2016.2

  Modified forms of citrus pectin possess anticancer properties. However, their mechanism of action and the structural features involved remain unclear. Here, we showed that citrus pectin modified by heat treatment displayed cytotoxic effects in cancer cells. A fractionation approach was used aiming to identify active molecules. Dialysis and ethanol precipitation followed by HPLC analysis evidenced that most of the activity was related to molecules with molecular weight corresponding to low degree of polymerization oligogalacturonic acid. Heat-treatment of galacturonic acid also generated cytotoxic molecules. Furthermore, heat-modified galacturonic acid and heat-fragmented pectin contained the same molecule that induced cell death when isolated by HPLC separation. Mass spectrometry analyses revealed that 4,5-dihydroxy-2-cyclopenten-1-one was one cytotoxic molecule present in heat-treated pectin. Finally, we synthesized the enantiopure (4R,5R)-4,5-dihydroxy-2-cyclopenten-1-one and demonstrated that this molecule was cytotoxic and induced a similar pattern of apoptotic-like features than heat-modified pectin. (C) 2015 Elsevier Ltd. All rights reserved.