spiro(3,4-dihydro-2H-1-benzopyran-2,1'-cyclohexane) | 4730-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro(3,4-dihydro-2H-1-benzopyran-2,1'-cyclohexane)
• 英文别名: spiro[cyclohexane-1,2'-chroman]；3,4-Dihydrospiro[1-benzopyran-2,1'-cyclohexane]；spiro[3,4-dihydrochromene-2,1'-cyclohexane]
• CAS: 4730-84-1
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: HUUUBGPZCYOCKH-UHFFFAOYSA-N

物化性质

• 沸点：
  80-82 °C(Press: 0.05 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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(3,4-dihydro-2H-1-benzopyran-2,1'-cyclohexane) 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 25.0~140.0 ℃ 、344.73 kPa 条件下， 反应 1.92h， 生成 5-(Spiro[3,4-dihydrochromene-2,1'-cyclohexane]-6-ylmethyl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

  摘要：

  A series of dihydrobenzofuran and dihydrobenzopyran thiazolidine-2,4-diones (compounds 3-26) was synthesized from the corresponding aryl aldehydes 1 in two steps. These compounds represent conformationally restricted analogues of the novel hypoglycemic ciglitazone. The series was evaluated by hypoglycemic effects in vitro by measuring stimulation of 2-deoxyglucose uptake in L6 myocytes and stimulation of expression of the glucose transporter protein in 3T3-L1 adipocytes. In vivo hypoglycemic effects were evaluated in the genetically obese ob/ob mouse, and structure-activity relationships are discussed. On the basis of this in vivo potency, we have selected the 2(R)-benzylbenzopyran derivative to be further studied in a clinical setting.

  DOI：

  10.1021/jm00105a050
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 spiro(3,4-dihydro-2H-1-benzopyran-2,1'-cyclohexane)
  参考文献：
  名称：

  A Facile Synthesis of Spirochromanes - 3,4-Dihydrospiro[2H-1-benzopyran-2,1′-cycloalkanes]

  摘要：

  DOI：

  10.1055/s-1980-29000

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。
• Reductive lithiation of cyclic benzofused ethers: a source of oxygen-functionalised organolithium compounds
  作者：Miguel Yus、Francisco Foubelo、José V Ferrández、Abderrazak Bachki

  DOI：10.1016/s0040-4020(02)00434-9

  日期：2002.6

  of an electrophile [E+=H2O, tBuCHO, PhCH2CHO, Ph(CH2)2CHO, PhCHO, furfural, Me2CO, Et2CO, cyclopentanone, cyclohexanone, cyclooctanone, (−)-menthone] in THF at −78°C gives, after hydrolysis, compounds 3. Some diols 3 are easily transformed into 2-substituted chromans 6 under acidic reaction conditions. The reductive lithiation of chroman (7) at 20°C for 3 h leads exclusively to the intermediate 8,

  2,3-二氢苯并呋喃（1）与锂和催化量的4,4'-二叔丁基联苯（DTBB，5％）在THF中于0°C反应1.5 h，然后添加亲电试剂THF中的[E + = H 2 O，t BuCHO，PhCH 2 CHO，Ph（CH 2）2 CHO，PhCHO，糠醛，Me 2 CO，Et 2 CO，环戊酮，环己酮，环辛酮，（-）-薄荷酮]水解后，-78℃得到化合物3。一些二醇3在酸性反应条件下容易转化为2-取代的苯并吡喃6。苯并二氢吡喃的还原锂化7）在20°C下反应3小时，仅生成中间体8，该中间体8是通过脱芳基形成的，并异构化为表面上更稳定的苄基中间体9。这些中间体与不同的亲电试剂E + = t BuCHO，PhCHO，糠醛，Me 2 CO，[CH 3（CH 2）4 ] 2 CO，环戊酮，环己酮，（-）-薄荷酮，Ph 2 CO}的反应，在-78℃下于THF中在水解后，导致区域异构体10和11的混合物。2,
• CANNONE P.; BELANGER D.; LEMAY G., SYNTHESIS, 1980, NO 4, 301-303
  作者：CANNONE P.、 BELANGER D.、 LEMAY G.

  DOI：——

  日期：——
• CLARK, DAVID A.;GOLDSTEIN, STEVEN W.;VOLKMANN, ROBERT A.;EGGLER, JAMES F.+, J. MED. CHEM., 34,(1991) N, C. 319-325
  作者：CLARK, DAVID A.、GOLDSTEIN, STEVEN W.、VOLKMANN, ROBERT A.、EGGLER, JAMES F.+

  DOI：——

  日期：——
• A Facile Synthesis of Spirochromanes - 3,4-Dihydrospiro[2<i>H</i>-1-benzopyran-2,1′-cycloalkanes]
  作者：P. Cannone、D. Bélanger、G. Lemay

  DOI：10.1055/s-1980-29000

  日期：——