(1S,2R,3R,5R)-2-ethoxycarbonyl-7,7-ethylenedioxy-3-hydroxy-bicyclo<3.3.0>octane | 70870-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,5R)-2-ethoxycarbonyl-7,7-ethylenedioxy-3-hydroxy-bicyclo<3.3.0>octane
• 英文别名: (1R,5S,6R,7R)-6-ethoxycarbonyl-3,3-ethylenedioxy-7-hydroxybicyclo<3.3.0>octane；(1R,5S,6R,7R)-3,3-ethylenedioxy-7-hydroxy-6-ethoxycarbonylbicyclo[3.3.0]octane；(1R,5S,6R,7R)-6-ethoxycarbonyl-3,3-ethylenedioxy-7-hydroxybicyclo[3.3.0]octane；ethyl (1'R,2'R,3'aR,6'aS)-2'-hydroxyspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-1'-carboxylate
• CAS: 70870-94-9
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: LBNNVWVPJWVUDR-LMLFDSFASA-N

物化性质

• 沸点：
  377.8±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,5R)-2-ethoxycarbonyl-7,7-ethylenedioxy-3-hydroxy-bicyclo<3.3.0>octane 在 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (1S,2R,3R,5R)-7-oxo-3-(tetrahydropyran-2-yl)oxy-2-[3(S)-(tetrahydropyran-2-yl)oxy-E-1-octenyl]bicyclo[3.3.0]octane
  参考文献：
  名称：

  A new synthesis of (+)-6a-carbaprostaglandin I2 employing yeast reduction of a β-keto ester derived from -bicyclo[3.3.0] octane-3,7-dione as the key-step

  摘要：

  DOI：

  10.1016/s0040-4020(01)87443-3
• 作为产物：
  描述：

  (1R,5S)-7,7-ethylenedioxy-2-ethoxycarbonylbicyclo[3.3.0]octan-3-one 以72%的产率得到
  参考文献：
  名称：

  MORI, KENJI;TSUJI, MASAHIRO, TETRAHEDRON, 44,(1988) N 10, 2835-2842

  摘要：

  DOI：

文献信息

• SYnthesis and absolute configuration of (−)-pentalenolactone E methyl ester
  作者：Kenji Mori、Masahiro Tsuji

  DOI：10.1016/s0040-4020(88)90019-1

  日期：1988.1

  synthesized as its levorotatory Me ester1 starting from (+)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one3, which was obtained by treating (±)-3 with baker's yeast. The absolute configuration of pentalenolactone E Me ester was established as depicted in1.

  从（+）-2-乙氧基羰基-7,7-乙撑二氧双环[3.3.0] octan-3-one 3出发，合成戊二酸内酯E的天然对映体，作为其左旋Me酯1，其通过处理（±）获得- 3与面包酵母。戊烯戊内酯E Me酯的绝对构型如图1所示。
• Optically active carbacyclin intermediates and processes for the
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04814468A1

  公开（公告）日：1989-03-21

  New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octane-3-on e, by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.

  新的中间体是一种光学活性的(1S,5R)-7,7-烷基二氧基-2-烷氧羰基-三环[3.3.0]辛-3-酮，可用于光学活性碳环前列腺素的合成。这种中间体是从外消旋化合物(1SR,5RS)-7,7-烷基二氧基-2-烷氧羰基-顺式-三环[3.3.0]辛烷-3-酮经微生物处理而制备的非还原化合物。该微生物具有特异性还原外消旋化合物的(1R,5S)异构体的酮基的能力。
• Optically active bicyclo[3.3.0]octane and processes for the preparation
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04871869A1

  公开（公告）日：1989-10-03

  New intermediate, an optically active (1R,5S,6S,7R)-6-tert-butyldiphenylsilyloxmethyl-7-hydroxy-bicyclo[3.3.0]oc tan-3-one (I) having high optical purity which is useful for the synthesis of an optically active carbacyclin and an optically active pentalenolactone E methyl ester. The compound (I) is also an intermediate compound serving for the purpose of improving the optical purity of (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane. The compound (I) is prepared by reacting (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane with tert-butylchlorodiphenylsilane in the presence of a base and removing the ethylenedioxy and tetrahydropyranyl groups of the resultant compound under an acid condition.

  新中间体化合物(I)是一种光学活性化合物，具有高光学纯度，可用于合成光学活性的碳环烯酸和光学活性的五环内酯E甲酯。化合物(I)还是一种中间体化合物，可用于提高(1R,5S,6S,7R)-3,3-乙二氧基-6-羟甲基-7-(2'-四氢呋喃基氧基)bicyclo[3.3.0]辛烷的光学纯度。化合物(I)通过在碱存在下反应(1R,5S,6S,7R)-3,3-乙二氧基-6-羟甲基-7-(2'-四氢呋喃基氧基)bicyclo[3.3.0]辛烷与叔丁基氯二苯基硅烷，然后在酸性条件下去除产物的乙二氧基和四氢呋喃基团而制备得到。
• MORI, KEHNDZI;TSUDZI, MASAXIRO
  作者：MORI, KEHNDZI、TSUDZI, MASAXIRO

  DOI：——

  日期：——
• US4814468A
  申请人：——

  公开号：US4814468A

  公开（公告）日：1989-03-21