(1S,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol | 324742-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol
• 英文别名: trans-1-hydroxymethyl-2-hydroxy-3-cyclopentene
• CAS: 324742-02-1
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: WBEXVFLBMXJLAO-RITPCOANSA-N

物化性质

• 沸点：
  207.5±28.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol 在 间氯过氧苯甲酸 作用下， 以97%的产率得到(1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  碳环利巴韦林及其类似物的对映选择性合成：线性与收敛方法

  摘要：

  描述了通过收敛和线性两种方法首次合成碳环利巴韦林的对映体。从手性非外消旋2-氮杂双环[2.2.1] hept-5-en-3-one获得的线性方法被证明是高效合成利巴韦林碳环类似物的途径。

  DOI：

  10.1016/s0040-4039(00)01704-4
• 作为产物：
  描述：

  (4R)-3-[[(1S,2S)-2-羟基-3-环戊烯-1-基]羰基]-4-(苯基甲基)-2-恶唑烷酮 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以83%的产率得到(1S,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol
  参考文献：
  名称：

  碳环利巴韦林及其类似物的对映选择性合成：线性与收敛方法

  摘要：

  描述了通过收敛和线性两种方法首次合成碳环利巴韦林的对映体。从手性非外消旋2-氮杂双环[2.2.1] hept-5-en-3-one获得的线性方法被证明是高效合成利巴韦林碳环类似物的途径。

  DOI：

  10.1016/s0040-4039(00)01704-4

文献信息

• [EN] STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING<br/>[FR] COMPOSÉS MODULATEURS DE STING, ET PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2019092660A1

  公开（公告）日：2019-05-16

  The present disclosure provides STING modulators/agonists, and methods of synthesis and methods for using for the prophylaxis or treatment of cancer and other STING-related diseases. The present disclosure relates to a compound represented by the Formula (I): wherein each symbol is as defined in the description, or a pharmaceutically acceptable salt thereof.

  本公开提供STING调节剂/激动剂，以及合成方法和用于预防或治疗癌症和其他STING相关疾病的方法。本公开涉及由式(I)表示的化合物：其中每个符号如描述中定义，或其药用可接受盐。
• N.sub.9 -cyclopentyl-substituted adenine derivatives having adenosine-2
  申请人：Ciba-Geigy Corporation

  公开号：US04954504A1

  公开（公告）日：1990-09-04

  The compound of the formula I ##STR1## wherein R, R.sub.3 and R.sub.5 independently represent hydrogen or hydroxy provided that at least one of R, R.sub.3 and R.sub.5 represents hydroxy; R.sub.1 represents hydrogen, lower alkyl, C.sub.3 -C.sub.7 -alkenyl, hydroxy-lower alkyl, optionally substituted cycloalkyl or optionally substituted cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, adamantyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydropyranyl-lower alkyl, tetrahydrothiopyranyl-lower alkyl, adamantyl-lower alkyl, aryl-hydroxy-lower alkyl, aryl, aryl-lower alkyl, aryl-C.sub.3 -C.sub.6 -cycloalkyl, 9-fluorenyl, 9-fluorenyl-lower alkyl or cycloalkenyl-lower alkyl; or R.sub.1 represents a bicyclic benzo-fused 5 or 6-membered saturated cyabocyclic radical or a benzo-fused 5 or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur directly attached to the fused benzene ring, any said bicyclic radicals being optionally substituted on the benzo portion by lower alkyl, lower alkoxy or halogen, or R.sub.1 represents any said bicyclic radical substituted-lower alkyl; R.sub.2 represents hydrogen, halogen, --S--R.sub.1 ', --NR.sub.b --R.sub.1 ', or --NH--R.sub.1 ' in each of which R.sub.1 ' has meaning as defined for R.sub.1 provided that R.sub.1 ' in --SR.sub.1 ' does not represent hydrogen; R.sub.b represents lower alkyl; R.sub.4 represents hydroxymethyl provided that R.sub.2 does not represent either hydrogen or --NHR.sub.1 ' in which R.sub.1 ' represents either hydrogen or lower alkyl; or R.sub.4 represents lower alkoxymethyl or lower alkylthiomethyl; or R.sub.4 represents --CONHR.sub.6 in which R.sub.6 represents lower alkyl; aryl-lower alkyl, C.sub.3 -C.sub.6 -cycloalkyl or hydroxy-lower alkyl; pharmaceutically acceptable ester derivatives thereof in which free hydroxy groups are esterified in form of a pharmaceutically acceptable ester; and pharmaceutically acceptable salts thereof; methods for their preparation; and their use as adenosine receptor agonists are disclosed.

  公式I的化合物如下：其中R、R.sub.3和R.sub.5独立地表示氢或羟基，但至少其中一个表示羟基；R.sub.1表示氢、较低的烷基、C.sub.3-C.sub.7-烯基、羟基-较低的烷基、可选地取代的环烷基或可选地取代的环烷基-较低的烷基、双环烷基、双环烷基-较低的烷基、金刚烷基、四氢吡喃基、四氢硫吡喃基、四氢吡喃基-较低的烷基、四氢硫吡喃基-较低的烷基、金刚烷基-较低的烷基、芳基-羟基-较低的烷基、芳基、芳基-较低的烷基、芳基-C.sub.3-C.sub.6-环烷基、9-芴基、9-芴基-较低的烷基或环烯基-较低的烷基；或R.sub.1表示一个双环苯并5或6-成员饱和环的腈状环基或一个苯并5或6-成员饱和杂环基，其中所述杂原子从氧和硫直接连接到融合苯环，任何所述双环基在苯部分上可选地被较低的烷基、较低的烷氧基或卤素取代，或R.sub.1表示任何所述双环基取代的较低烷基；R.sub.2表示氢、卤素、--S--R.sub.1 '、--NR.sub.b--R.sub.1 '或--NH--R.sub.1'，其中在每个中R.sub.1'的含义如R.sub.1所定义，但在--SR.sub.1'中，R.sub.1'不表示氢；R.sub.b表示较低的烷基；R.sub.4表示羟甲基，但当R.sub.2不表示氢或--NHR.sub.1'时，其中R.sub.1'表示氢或较低的烷基；或R.sub.4表示较低的烷氧甲基或较低的烷硫甲基；或R.sub.4表示--CONHR.sub.6，其中R.sub.6表示芳基-较低的烷基、C.sub.3-C.sub.6-环烷基或羟基-较低的烷基；还公开了其药学上可接受的酯衍生物，其中游离羟基以药学上可接受的酯形式酯化，以及其药学上可接受的盐；公开了其制备方法；以及其作为腺苷受体激动剂的用途。
• N9-cyclopentyl-substituted adenine derivatives
  申请人：CIBA-GEIGY AG

  公开号：EP0267878A1

  公开（公告）日：1988-05-18

  The compounds of the formula I wherein R, R3 and R5 independently represent hydrogen or hydroxy provided that at least one of R, R3 and R5 represents hydroxy; R1 represents hydrogen, lower alkyl, C3-C7alkenyl, hydroxy-lower alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-lower alkyl, 2-norbornyl, 2-norbornyl-lower alkyl, aryl, aryl-lower alkyl, aryl-C3-C6cycloalkyl, 9-fluorenyl or 9-fluorenyl-lower alkyl; or R1 represents a bicyclic benzo-fused 5 or 6-membered saturated carbocyclic radical or a benzo fused 5 or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur directly attached to the fused benzene ring, any said bicyclic radicals being optionally substituted on the benzo portion by lower alkyl, lower alkoxy or halogen; R2 represents hydrogen, halogen, -SR1 or -N(R9)R1 in each of which R1 has meaning as defined hereinbefore provided that R1 in -SR1 does not represent hydrogen; R9 represents hydrogen or lower alkyl; R4 represents hydroxymethyl provided that R2 does not represent either hydrogen or -NHRI in which R1 represents either hydrogen or lower alkyl; or R4 represents lower alkoxymethyl, lower alkylthiomethyl or -CONHR6 in which R6 represents lower alkyl, aryl-lower alkyl, C3-Cscycloalkyl or hydroxy-lower alkyl; pharmaceutically acceptable ester derivatives thereof in which free hydroxy groups are esterified in form of a pharmaceutically acceptable ester; and salts thereof; methods for their preparation; and their use as adenosine receptor agonists are disclosed.

  式 I 的化合物 其中R、R3和R5独立地代表氢或羟基，但R、R3和R5中至少有一个代表羟基；R1代表氢、低级烷基、C3-C7烯基、羟基-低级烷基、C3-C6环烷基、C3-C6环烷基-低级烷基、2-降冰片基、2-降冰片基-低级烷基、芳基、芳基-低级烷基、芳基-C3-C6环烷基、9-芴基或9-芴基-低级烷基；或 R1 代表双环苯并 5 或 6 元饱和碳环基，或苯并 5 或 6 元饱和杂环基，其中含有一个选自氧和硫的杂原子，直接连接到苯并环上，任何上述双环基的苯并部分可选择被低级烷基、低级烷氧基或卤素取代；R2 代表氢、卤素、-SR1 或-N(R9)R1，其中每个 R1 的含义如前文所定义，条件是 -SR1 中的 R1 不代表氢；R9 代表氢或低级烷基；R4 代表羟甲基，条件是 R2 不代表氢或-NHRI，其中 R1 代表氢或低级烷基；或R4代表低级烷氧基甲基、低级烷硫基甲基或-CONHR6，其中R6代表低级烷基、芳基-低级烷基、C3-Cscycloalkyl或羟基-低级烷基；公开了其药学上可接受的酯衍生物，其中游离羟基以药学上可接受的酯的形式酯化；及其盐；其制备方法；及其作为腺苷受体激动剂的用途。
• PALMER, CHRISTOPHER F.;PARRY, KEITH P.;ROBERTS, STANLEY M., TETRAHEDRON LETT., 31,(1990) N, C. 279-282
  作者：PALMER, CHRISTOPHER F.、PARRY, KEITH P.、ROBERTS, STANLEY M.

  DOI：——

  日期：——
• PROCESS FOR PREPARING A CHIRAL NUCLEOSIDE ANALOGUE
  申请人：GLAXO GROUP LIMITED

  公开号：EP1032573A1

  公开（公告）日：2000-09-06