(4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol | 369647-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol
• 英文别名: 1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 369647-26-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: AUSCOWHRXXYTPI-SXNZSPLWSA-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：

  (4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol 在 Grubbs catalyst first generation 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以87%的产率得到(+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one
  参考文献：
  名称：

  （-）-oleocanthal的绝对构型的合成和分配：一种来自天然初榨橄榄油的有效，天然存在的非甾体类抗炎和抗氧化剂。

  摘要：

  [结构：见正文]有效的全合成和油酸双酚1（又称脱乙酰氧基葡糖苷糖苷配基）的（+）-和（-）-对映体的绝对构型分配，后者是从特级初榨橄榄油衍生而来的，已经实现了负责橄榄油的喉咙刺激特性的背部。天然对映异构体（-）-1的绝对和相对立体化学被证明是3S，4E。两种合成均以d-（-）-核糖开始，分12步进行，总产率为7％。两种对映异构体均被证明是非甾体类抗炎药和抗氧化剂。

  DOI：

  10.1021/ol052106a
• 作为产物：
  描述：

  (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 在 sodium periodate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Improved and alternative synthesis of d- and l-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00316-6

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。
• Practical Synthesis of <scp>d</scp>- and <scp>l</scp>-2-Cyclopentenone and Their Utility for the Synthesis of Carbocyclic Antiviral Nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus)
  作者：Yun H. Jin、Peng Liu、Jianing Wang、Robert Baker、John Huggins、Chung K. Chu

  DOI：10.1021/jo034999v

  日期：2003.11.1

  Highly efficient and practical methodology for the syntheses of D- and l-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for the synthesis of carbocyclic nucleosides, have been developed via a ring-closing metathesis reaction from d-ribose in eight steps. The utility of D- and l-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for the preparation

  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。
• Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues
  作者：Amos B. Smith、Jeffrey B. Sperry、Qiang Han

  DOI：10.1021/jo071146k

  日期：2007.8.31

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.
• 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
• Synthesis and biological evaluation of cyclopentyl-triazolol-pyrimidine (CPTP) based P2Y12 antagonists
  作者：Wangyang Tu、Jiang Fan、Haitang Zhang、Guoji Xu、Zhiwei Liu、Jian Qu、Fanglong Yang、Lei Zhang、Tianyu Luan、Jijun Yuan、Aishen Gong、Jun Feng、Piaoyang Sun、Qing Dong

  DOI：10.1016/j.bmcl.2013.11.055

  日期：2014.1

  In this Letter we describe SAR investigation on the cyclopentyl-triazolol-pyrimidine scaffold in pursuit of new oral P2Y(12) inhibitors. Different synthetic routes were developed for variations at the cyclopentyl core. Optimization finally led to compound 2d which was advanced into preclinical development based on better potency and safety profile in comparison to ticagrelor. (C) 2013 Elsevier Ltd. All rights reserved.