(1S)-1-((4S,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol | 369647-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-((4S,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol
• 英文别名: (1S,2S,3R)-(-)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-(S)-2-propen-1-ol；(-)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol；(1S)-(4S,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol；(1S,2S,3R)-(-)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)-prop-2-en-1-ol；(1S,2S,3R)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)-(S)-prop-2-en-1-ol；(1S)-1-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 369647-25-6
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: AUSCOWHRXXYTPI-YIZRAAEISA-N

物化性质

• 沸点：
  256.6±30.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (1S)-1-((4S,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol 在 Grubbs catalyst first generation 、 manganese(IV) oxide 、 potassium tert-butylate 、 仲丁基锂 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 50.5h， 生成 (3aR,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one
  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
• 作为产物：
  描述：

  (R)-1-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 在 sodium periodate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (1S)-1-((4S,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol
  参考文献：
  名称：

  D-和l-2-环戊烯酮的实用合成及其在合成抗正痘病毒（天花，猴痘和牛痘病毒）的碳环抗病毒核苷中的用途。

  摘要：

  通过闭环易位反应，开发了用于合成D-和1-4,5-O-异亚丙基-2-环戊烯酮（9和22）（合成碳环核苷的通用中间体）的高效实用方法八个步骤从d-核糖中提取。D-和1-4,5-O-异亚丙基-2-环戊烯酮在制备D-环戊基-6-氮杂嘧啶12和D-环戊烯基-5-卤代胞嘧啶核苷中的应用证明了其实用性（33-35）使用Mitsunobu反应引入嘧啶碱基作为潜在的抗病毒剂。描述了对合成核苷的正痘病毒（天花，猴痘和牛痘病毒）的初步抗病毒活性。

  DOI：

  10.1021/jo034999v

文献信息

• Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides
  作者：Julie Broggi、Hiroki Kumamoto、Sabine Berteina-Raboin、Steven P. Nolan、Luigi A. Agrofoglio

  DOI：10.1002/ejoc.200801124

  日期：——

  A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(–)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assistedHuisgen 1,3-dipolar cycloaddition. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  报道了一种重新审视和改进的光学活性叠氮基碳核苷的合成。这种叠氮基前体用于通过铜 (I) 催化和微波辅助的 Huisgen 1,3-偶极分子成功且通用地合成对映体纯 D-(–)-1,4-二取代的 1,2,3-三唑基碳核苷环加成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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.
• Improved and alternative synthesis of d- and l-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides
  作者：Hyung Ryong Moon、Won Jun Choi、Hea Ok Kim、Lak Shin Jeong

  DOI：10.1016/s0957-4166(02)00316-6

  日期：2002.6

  Improved and alternative syntheses Of D- and L-cyclopentenone derivatives were achieved in six steps from D-ribose via ring-closing metathesis (RCM) reaction as a key step. These derivatives serve as very versatile intermediates for the synthesis of carbocyclic nucleosides. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Syntheses of <scp>d</scp>- and <scp>l</scp>-Cyclopentenone Derivatives Using Ring-Closing Metathesis:  Versatile Intermediates for the Synthesis of <scp>d</scp>- and <scp>l</scp>-Carbocyclic Nucleosides
  作者：Won Jun Choi、Jae Gyu Park、Su Jeong Yoo、Hea Ok Kim、Hyung Ryong Moon、Moon Woo Chun、Young Hoon Jung、Lak Shin Jeong

  DOI：10.1021/jo015733w

  日期：2001.9.1
• WO2008/124157
  申请人：——

  公开号：——

  公开（公告）日：——