(R)-3-(hydroxymethyl)cyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(hydroxymethyl)cyclopentanone
• 英文别名: 3R-(hydroxymethyl)cyclopentanone；(3R)-3-(Hydroxymethyl)cyclopentan-1-one
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: ZUDJASYMJNCZKF-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-(hydroxymethyl)cyclopentanone 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 苯基氯化硒 、 cerium(III) chloride 、 lithium diisopropyl amide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 (1S*,4S*)-4-(t-butyldimethylsilyloxy)methyl-2-cyclopentenol
  参考文献：
  名称：

  碳环核苷的简洁对映选择性途径：卡博韦碳环部分的不对称合成

  摘要：

  摘要 (-)-Trans-4-t-丁基二甲基甲硅烷氧基甲基-2-环戊烯醇 (13) 是合成 (-)-卡波韦 (15) 的关键中间体，通过使用手性 α-重氮基的对映选择性双环结构合成。由醋酸铑 (II) 催化的 β-酮酯 3。

  DOI：

  10.1080/00397919708004098
• 作为产物：
  描述：

  (R)3-氧代环戊烷羧酸 在 盐酸 、 lithium aluminium tetrahydride 、 水 、 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 (R)-3-(hydroxymethyl)cyclopentanone
  参考文献：
  名称：

  Synthesis and Biological Activity of Bimorpholine and its Carbanucleoside

  摘要：

  A new enantiomerically pure carbacyclic nucleoside analogue with bimorpholine as a nonaromatic nucleobase was synthesized. The nucleoside analogue and bimorpholine were tested for cytotoxicity using an MTT assay and the xCELLigence System. Both assays revealed that compound 3 was highly cytotoxic at a 50 mu M concentration while the cytotoxic effect of compound 1 was much less prominent. No antiretroviral activity was detected for this compound. In contrast, it acted as a potent inhibitor of hepatitis C virus (HCV) replication. Most likely this effect originates largely from the cytotoxicity of the compound; however, it is possible that a specific mechanism of HCV inhibition also exists.

  DOI：

  10.1080/15257770.2011.621919

文献信息

• SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20130023502A1

  公开（公告）日：2013-01-24

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R 1 , R 2 , R 4 , R 3 , R 5 and R 6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶化合物， 其中环A是一个含有五个成员的饱和或不饱和碳环，该环可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组成， 其中R1、R2、R4、R3、R5和R6如权利要求书中所定义，并且环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药用盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• Synthesis of <scp>d</scp>- and <scp>l</scp>-Carbocyclic Nucleosides via Rhodium-Catalyzed Asymmetric Hydroacylation as the Key Step
  作者：Patricia Marcé、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1021/ol801791g

  日期：2008.11.6

  D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective rhodium/duphos-catalyzed hydroacylation reaction as the key step. The 3-hydroxymethyl-cyclopentanol intermediate was obtained by stereoselective reduction of ketone and by dynamic kinetic resolution (DKR).

  D-和L-碳环核苷是通过新方法获得的，该方法涉及对映体选择性的铑/二聚膦酸酯催化的加氢酰化反应为关键步骤。通过立体选择性地还原酮和通过动态动力学拆分（DKR）获得3-羟甲基-环戊醇中间体。
• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS
  申请人：QIAN Xiangping

  公开号：US20120135964A1

  公开（公告）日：2012-05-31

  Chemical entities that modulate smooth muscle myosin and/or non-muscle myosin, pharmaceutical compositions and methods of treatment of diseases and conditions associated with smooth muscle myosin and/or non-muscle myosin are described.

  本文描述了调节平滑肌肌球蛋白和/或非肌肉肌球蛋白的化学实体、制药组合物和治疗与平滑肌肌球蛋白和/或非肌肉肌球蛋白相关的疾病和病状的方法。
• Posner, Gary H.; Weitzberg, Moshe; Jew, Sang-sup, Synthetic Communications, 1987, vol. 17, # 6, p. 611 - 620
  作者：Posner, Gary H.、Weitzberg, Moshe、Jew, Sang-sup

  DOI：——

  日期：——
• ANTIVIRAL NUCLEOSIDE ANALOGS
  申请人：Babu Yarlagadda S.

  公开号：US20100015094A1

  公开（公告）日：2010-01-21

  The invention provides compounds of Formula (I), as described herein, as well as pharmaceutical compositions comprising the compounds, and synthetic methods and intermediates that are useful for preparing the compounds. The compounds of Formula (I) are useful as anti-viral agents and/or as anti-cancer agents.