Spiro-(benzofuran-2(3H),1'-cyclohexan) | 182-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Spiro-(benzofuran-2(3H),1'-cyclohexan)
• 英文别名: Spiro(benzofuran-2(3H),1'-cyclohexane)；spiro[3H-1-benzofuran-2,1'-cyclohexane]
• CAS: 182-50-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: NBRDIJDCPCLUPB-UHFFFAOYSA-N

物化性质

• 沸点：
  296.8±10.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  Spiro-(benzofuran-2(3H),1'-cyclohexan) 在 N-氯代丁二酰亚胺 、 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.0h， 生成 N-[(8S)-1-氮杂双环[2.2.2]辛烷-8-基]-5-氯螺[3H-1-苯并呋喃-2,1'-环己烷]-7-甲酰胺
  参考文献：
  名称：

  开发高亲和力的5-HT3受体拮抗剂。1.新型苯甲酰胺的初始结构-活性关系。

  摘要：

  该报告描述了新型的苯甲酰胺的开发，这些新型的苯甲酰胺是口服活性，高效的5-HT3受体特异性拮抗剂。在该第一份报告中描述的是结构-活性关系，该关系导致了具有改进的效价和选择性的新型结构。从这一系列化合物中，鉴定并选择了（S）-28作为5-HT3受体拮抗剂进行进一步评估。与5-HT3拮抗剂（例如GR 38032F，BRL 43694和甲氧氯普胺）相比，（S）-28在（a）抑制大鼠内嗅皮质中与5-HT3受体结合位点的结合中最活跃，Ki值为0.19 nM，并且（b）用确定为9微克/千克po的ED50值阻断雪貂中顺铂引起的呕吐。

  DOI：

  10.1021/jm00083a014
• 作为产物：
  描述：

  1-(氯甲基)环己烯 在 盐酸 、 Amberlist 15 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 Spiro-(benzofuran-2(3H),1'-cyclohexan)
  参考文献：
  名称：

  简短高效的grisan合成

  摘要：

  描述了使用甲氧基甲氧基苯和1-氯甲基环己烯为起始原料的三步合成grisan（螺[苯并呋喃-2（3 H）-1'-环己烷]）。

  DOI：

  10.1002/jhet.5570260371

文献信息

• Montmorillonite-mediated hetero-Diels–Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols
  作者：Kazuhiro Chiba、Tetsuya Hirano、Yoshikazu Kitano、Masahiro Tada

  DOI：10.1039/a900657e

  日期：——

  The intermolecular hetero-Diels–Alder reaction of in situ-generated o-quinomethanes and unactivated alkenes has been accomplished through a wet montmorillonite catalyst in a LiClO4–MeNO2 solution to give good yields of varied chromane skeletons.

  通过湿蒙脱土催化剂在LiClO4-MeNO2溶液中实现了原位生成的邻醌甲烷与未活化烯烃的分子间杂Diels-Alder反应，得到了多种色满骨架化合物的良好产率。
• New homologation of 2-hydroxy and 2-mercapto benzylic alcohols
  作者：Prabir K. Choudhury、Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1016/s0040-4020(97)10161-2

  日期：1997.12

  or benzo-1,3-oxathianes 1 [easily prepared from 2-hydroxy or 2-mercapto benzylic alcohols (3 or 4, respectively) and carbonyl compounds] with an excess of lithium and a catalytic amount of DTBB (4.5 mol %) in THF at room temperature or −78°C leads, after hydrolysis with water, to the corresponding homobenzylic alcohols 2. Cyclisation of compounds 2 under acidic (85% H3PO4) or neutral (Ph3P/DIAD) conditions

  苯并-1,3-二恶烷或苯并-1,3-氧杂蒽1 [由2-羟基或2-巯基苄基醇（分别为3或4）和羰基化合物容易制得]与过量的锂和α在室温或-78°C下，DTBB在THF中的催化量（4.5摩尔％）导致水解后生成相应的均苄醇2。在酸性（85％H 3 PO 4）或中性（Ph 3 P / DIAD）条件下将化合物2环化，可得到预期的杂环5。
• HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF
  申请人：Chytil Milan

  公开号：US20120077802A1

  公开（公告）日：2012-03-29

  Provided herein are spiro-cyclic compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including, e.g., neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as, e.g., histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical compositions containing the compounds and their methods of use are also provided herein.

  本文提供了螺环化合物的合成方法和使用方法。所提供的化合物可用于治疗、预防和/或管理各种疾病，包括神经系统疾病和代谢性疾病等。本文提供的化合物抑制组胺H3受体的活性，并调节各种神经递质的释放，例如组胺、乙酰胆碱、去甲肾上腺素和多巴胺（例如在突触处）。本文还提供了含有这些化合物的制药组合物及其使用方法。
• Synthesis of 2,3-Dihydrobenzofurans by Mn(OAc)₃-Based Oxidative Cycloaddition of 2-Cyclohexenones with Alkenes. Synthesis of (±)-Conocarpan
  作者：Barry B. Snider、Luning Han、Chaoyu Xie

  DOI：10.1021/jo9708506

  日期：1997.10.1

  Oxidative cycloaddition of a 2-cyclohexenone or alpha-tetralone and an alkene with dried Mn(OAc)(3) in benzene at 80-140 degrees C provides a general route to dihydrobenzofurans 15 and dihydronaphthofurans 17. Although the yields are modest, this one-pot reaction provides simple access to these compounds, which have previously been prepared by multistep routes. Oxidative cycloaddition of 2-cyclohexenones with beta-methylstyrenes provides a new route to benzofuranoid neolignans, which was applied to the synthesis of conocarpan (22). The formation of 2-acetoxyhexanedioic acids 27 and 47 from acetoxylation of 2-cyclohexenones in HOAc, but not in benzene, opens up a new class of Mn(OAc)(3) reactions and explains Watt and Demir's discovery that much higher yields of alpha'-acetoxy enones are obtained in benzene than in HOAc.
• Pd(II)-Catalyzed Hydroxyl-Directed C−H Activation/C−O Cyclization: Expedient Construction of Dihydrobenzofurans
  作者：Xisheng Wang、Yi Lu、Hui-Xiong Dai、Jin-Quan Yu

  DOI：10.1021/ja105366u

  日期：2010.9.8

  A Pd(II)-catalyzed C-H activation/C-O cyclization reaction directed by a proximate hydroxyl group has been developed. This reaction provides a new method for constructing dihydrobenzofurans, including spirocyclic analogues, a process that is potentially applicable to natural product synthesis.