cis-8-oxabicyclo<4.3.0>nonane | 1158650-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: cis-8-oxabicyclo<4.3.0>nonane
• 英文别名: cis-2-oxahydrindane；cis-Hexahydro-phthalan；cis-8-Oxabicyclo[4.3.0]nonane；(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzofuran
• CAS: 1158650-41-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: HGQBCKVFVUCIML-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-8-oxabicyclo<4.3.0>nonane 在 氢溴酸 、 三溴化磷 作用下， 生成 cis-1,2-bis(bromomethyl)cyclohexane
  参考文献：
  名称：

  The decomposition of saturated oxygen-, nitrogen-, and sulfur-containing heterocyclic and acyclic compounds by phosphorus halides

  摘要：

  DOI：

  10.1007/bf00951712
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酰氯 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 cis-8-oxabicyclo<4.3.0>nonane
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403

文献信息

• Organotins as etherification catalysts. III. Etherifications and hydro-hydroxy-eliminations promoted by butyltin trichloride
  作者：Daniele Marton、Pierangelo Slaviero、Giuseppe Tagliavini

  DOI：10.1016/s0040-4020(01)89178-x

  日期：——

  Butyltin trichloride, as a catalyst precursor, promotes the following processes: (i) etherification of 2,3-unsaturated alcohols, (ii) etherification of functional diols, (iii) cyclization of 2,5-hexanedione, and (iv) dehydration of cyclic diols. Many examples are reported.

  丁基锡三氯化物作为催化剂前体，可促进以下过程：（i）2,3-不饱和醇的醚化，（ii）功能性二醇的醚化，（iii）2,5-己二酮的环化和（iv）脱水环状二醇。报告了许多示例。
• Intramolecular Condensation of 1,2-C₆H₄(CH₂RH)₂(R = O, S, and NH) to Yield Heterocyclic Compounds over Halide-cluster Catalysts
  作者：Sayoko Nagashima、Satoshi Kamiguchi、Kentaro Kudo、Tomoaki Sasaki、Teiji Chihara

  DOI：10.1246/cl.2011.78

  日期：2011.1.5

  1,2-Benzenedimethanol was reacted under a helium stream in the presence of [(Nb6Cl12)Cl2(H2O)4]·4H2O supported on silica gel. When the temperature was raised above 200 °C, catalytic activity of the...

  1,2-苯甲醇在[(Nb6Cl12)Cl2(H2O)4]·4H2O 存在下，在氦气流下反应在硅胶上。当温度升高到 200°C 以上时，催化剂的催化活性...
• PREPARATION OF (3aS,7aR)-HEXAHYDROISOBENZOFURAN-1(3H)-ONE BY CATALYZED BIOLOGICAL RESOLUTION OF DIMETHYL CYCLOHEXANE-1,2-DICARBOXYLATE
  申请人：Lloyd Michael Charles

  公开号：US20130273618A1

  公开（公告）日：2013-10-17

  Processes for the synthesis of (3aS,7aR)-hexahydroisobenzofuran-1-(3H)-one, comprising comprising enzymatic hydrolysis of dimethyl cyclohexane-1,2-dicarboxylate to form (1S,2R)-2-(methoxycarbonyl) cyclohexanecarboxylic acid. The enzyme can be from a non-mammalian source.

  合成(3aS,7aR)-六氢异苯并呋喃-1-(3H)-酮的过程，包括酶解二甲基环己烷-1,2-二甲酸酯形成(1S,2R)-2-(甲氧羰基)环己烷羧酸。该酶可以来自非哺乳动物来源。
• Benzothiophene estrogen receptor modulators
  申请人：G1 Therapeutics, Inc.

  公开号：US10208011B2

  公开（公告）日：2019-02-19

  This invention is a benzothiophene estrogen receptor modulator or its pharmaceutically acceptable salt or a pharmaceutically acceptable composition thereof to treat an estrogen-related medical disorder.

  本发明是一种苯并噻吩雌激素受体调节剂或其药学上可接受的盐或其药学上可接受的组合物，用于治疗与雌激素相关的疾病。
• Scope of alkoxymethyl radical cyclizations
  作者：Viresh H. Rawal、Surendra P. Singh、Claire Dufour、Christophe Michoud

  DOI：10.1021/jo00079a016

  日期：1993.12

  We have explored different aspects of the cyclization capability of alkoxymethyl radicals and report here a full account of our investigations. The required radicals were generated from (phenylseleno)methyl ethers (e.g., 6), which were prepared from homoallylic or bis-homoallylic alcohols by a two-step process. The alcohols were alkylated with (iodomethyl)tributylstannane. The stannanes were reacted with n-BuLi, and the resulting alpha-alkoxyanions were trapped with diphenyldiselenide to give the (phenylseleno)methyl ethers, which were stable to chromatography. When treated with tributyltin hydride, in the presence of a radical initiator, these precursors undergo a smooth cyclization to substituted tetrahydrofurans and tetrahydropyrans. Formation of the cyclization product was found to be the primary pathway even at relatively high tin hydride concentration. The diastereoselectivity of this cyclization was comparable to that observed in other radical cyclizations. The cis selectivity in cyclization of 6 increased gradually (up to 11:1) as the reaction temperature was lowered. The cyclization can be used for the synthesis of bicyclic and tricyclic compounds and can be incorporated in systems capable of tandem cyclizations.