4-叔丁基环己酮二苄基缩醛 | 88278-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-叔丁基环己酮二苄基缩醛
• 英文名称: 4-tert-butylcyclohexanone dibenzyl acetal
• 英文别名: (4-tert-butyl-1-phenylmethoxycyclohexyl)oxymethylbenzene
• CAS: 88278-94-8
• 化学式: C₂₄H₃₂O₂
• 分子量: 352.517
• InChiKey: QVGZTDVZZAXOLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.4±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-叔丁基环己酮二苄基缩醛 生成 methyl 4-(4-tert-butyl-1-phenylmethoxycyclohexyl)-4-oxobutanoate
  参考文献：
  名称：

  Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods

  摘要：

  DOI：

  10.1021/ja00318a035
• 作为产物：
  描述：

  4-叔丁基环己酮 、 苯甲醇 在 camphor-10-sulfonic acid 作用下， 以 环己烷 为溶剂， 反应 12.0h， 以77%的产率得到4-叔丁基环己酮二苄基缩醛
  参考文献：
  名称：

  硫代烷基苄基醚的[1，2] -Wittig重排，碳负离子C原子上的构型反转。李环己基的立体选择性减少+芳烃-

  摘要：

  非对映体O，硒缩酮的治疗顺或-反式- 4与锂萘基提供，通过立体选择性还原的自由基中间体的5中，沿轴向锂化环己基醚反式- 6。反式- 6得到平展苄环己醇的顺式- 5后立体选择性[1,2] -Wittig重排和含水后处理。

  DOI：

  10.1016/s0040-4039(00)60571-3

文献信息

• Remarkable equatorial selectivity in the aldol coupling between enol silyl ethers and cyclohexanone acetals
  作者：Eiichi Nakamura、Yoshiaki Horiguchi、Jun-ichi Shimada、Isao Kuwajima

  DOI：10.1039/c39830000796

  日期：——

  Lewis acid-catalysed aldol coupling of enol silyl ethers and substituted cyclohexanone acetals shows a markedly higher ratio of equatorial attack than the reaction of the parent ketones.

  路易斯酸催化的烯醇甲硅烷基醚和取代的环己酮缩醛的醛醇缩合反应显示出比母体酮的反应明显更高的赤道侵蚀率。
• Geminal Acylation with Methyl-Substituted Analogues of 1,2-Bis[(trimethylsilyl)oxy]cyclobutene
  作者：Sheldon N. Crane、Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo971055v

  日期：1997.12.1

  BF3 . Et2O-catalyzed geminal acylation of ketones and acetals with 3-methyl-1,2-bis[(trimethylsilyl)oxy)]cyclobutene (3) provided methylcyclopentanediones in yields that ranged from 40 to 94%. The best substrates were unhindered cyclohexanones. With acetals, stereochemical preferences in the initial Mukaiyama-like aldol step giving cyclobutanones translated into the stereochemistry of the ultimate cyclopentanedione products. With ketones, equilibration of the initial cyclobutanone compounds resulted in cyclopentanedione products with a different stereochemical preference. The gem-dimethylcyclobutene reagent 4 reacted with ketones to give gem-dimethylcyclopentanediones in modest yield. The process was much more stereochemically efficient than the reaction with 3. Rearrangement from the initial cyclobutanone compound was partially diverted toward air-sensitive 3-furanone compounds and ring-opened 1,2-diones. Only furanones (e.g., 52 and 53) were isolated from reactions with the tetramethylcyclobutene 51.
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——