6,9-Dimethoxy-1,1-dimethyl-2,3-dihydrophenanthren-4-one | 111948-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6,9-Dimethoxy-1,1-dimethyl-2,3-dihydrophenanthren-4-one
• CAS: 111948-76-6
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: JRHYDYDFPFYOFK-UHFFFAOYSA-N

物化性质

• 沸点：
  458.2±45.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,9-Dimethoxy-1,1-dimethyl-2,3-dihydrophenanthren-4-one 在 氢氧化钾 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 17.0h， 生成 Methyl 2-(5-diazo-2-methyl-4-oxopentan-2-yl)-4,7-dimethoxynaphthalene-1-carboxylate
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal

  摘要：

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.089
• 作为产物：
  描述：

  1,1-dimethyl-6,9-dimethoxy-1,2,3,4-tetrahydrophenanthrene 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到6,9-Dimethoxy-1,1-dimethyl-2,3-dihydrophenanthren-4-one
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal

  摘要：

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.089

文献信息

• Reductive methylation of α-naphthyl ketones stereocontrolled synthesis of -octahydrophenanthrenes related to diterpenes
  作者：Sukanta Bhattacharyya、Tapan K Karpha、Basudeb Basu、Debabrata Mukherjee

  DOI：10.1016/s0040-4039(00)85197-7

  日期：1986.1

  Reductive methylation of the tricyclic ketones and with lithium in liquid ammonia afforded the β,γ-unsaturated ketones and respectively which were stereoselectively converted into the corresponding A/B -fused ketones and .

  将三环酮还原甲基化并用锂在液氨中还原生成β，γ-不饱和酮，并分别立体选择性地转化为相应的A / B稠合的酮和。
• BHATTACHARYYA, SUKANTA;GHOSAL, MANUKA;MUKHERJEE, DEBABRATA, TETRAHEDRON LETT., 28,(1987) N 21, 2431-2432
  作者：BHATTACHARYYA, SUKANTA、GHOSAL, MANUKA、MUKHERJEE, DEBABRATA

  DOI：——

  日期：——
• Stereocontrolled synthesis of xanthoperyl methyl ether
  作者：Sukanta Bhattacharyya、Manuka Ghosal、Debabrata Mukherjee

  DOI：10.1016/s0040-4039(00)96144-6

  日期：——
• Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal
  作者：Lokesh Chandra Pati、Debabrata Mukherjee

  DOI：10.1016/j.tetlet.2004.10.089

  日期：2004.12

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.