1,1-bis(4-hydroxyphenyl)-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]propene | 1219610-77-1

• 英文名称: 1,1-bis(4-hydroxyphenyl)-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]propene
• CAS: 1219610-77-1
• 化学式: C₄₈H₃₇CoO₂
• 分子量: 704.814
• InChiKey: XYFKLXOONYBKOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  246 °C

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,1-bis(4-hydroxyphenyl)-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]propene 、 2-氯-N,N-二甲基乙胺 在 K₂CO₃ 作用下， 以 水 、 丙酮 为溶剂， 以39%的产率得到Z,E-1-(4-hydroxyphenyl)-1-[4-(2-dimethylaminoethoxy)phenyl]-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]propene
  参考文献：
  名称：

  Organometallic SERMs (selective estrogen receptor modulators): Cobaltifens, the (cyclobutadiene)cobalt analogues of hydroxytamoxifen

  摘要：

  The McMurry coupling of (tetraphenylcyclobutadiene)cobalt(cyclopentadienyl) ketones, (C4Ph4)Co[C5H4C(=O)R], where R = Me, 3a, or Et, 3b, with a range of substituted benzophenones furnished a series of cobaltifens, organometallic analogues of tamoxifen whereby a phenyl ring has been replaced by an organo-cobalt sandwich moiety. These systems of the general formula (eta(4)-C4Ph4)Co[eta(5)-C5H4C(R)=C(Ar)Ar'], where R = Me or Et, and Ar = Ar' = p-C6H4X where X is OH, 2a and 2b, OMe, 2c and 2d, OBn, 2e and 2f, or O(CH2)(2)NMe2, 12a and 12b, and where Ar = C6H4OH and Ar' = C6H4O(CH2)(2)NMe2, 2g and 2h, have been characterised by NMR spectroscopy and/or X-ray crystallography. The effect of 2a and 2b, 2g and 2h, and 12a and 12b on the growth of MCF-7 (hormone-dependent) and MDA-MB-231 (hormone-independent breast cancer cells) was studied. The dihydroxycobaltifens 2a and 2b exhibit a strong estrogenic effect on MCF-7 cells while the aminoalkyl-hydroxycobaltifens, 2g and 2h, were found to be only slightly cytotoxic on MDA-MB-231 cells (IC50 = 27.5 and 17 mu M); surprisingly, however, the bis-(dimethylaminoethoxy) cobaltifens, 12a and 12b were shown to be highly cytotoxic towards both cell lines (IC50 = 3.8 and 2.5 mu M). (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.11.003
• 作为产物：
  描述：

  [(η⁵-acetylcyclopentadienyl)(η⁴-tetraphenylcyclobutadiene)cobalt] 、 4,4'-二羟基二苯甲酮 在 TiCl₄ 、 Zn 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1,1-bis(4-hydroxyphenyl)-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]propene
  参考文献：
  名称：

  Organometallic SERMs (selective estrogen receptor modulators): Cobaltifens, the (cyclobutadiene)cobalt analogues of hydroxytamoxifen

  摘要：

  The McMurry coupling of (tetraphenylcyclobutadiene)cobalt(cyclopentadienyl) ketones, (C4Ph4)Co[C5H4C(=O)R], where R = Me, 3a, or Et, 3b, with a range of substituted benzophenones furnished a series of cobaltifens, organometallic analogues of tamoxifen whereby a phenyl ring has been replaced by an organo-cobalt sandwich moiety. These systems of the general formula (eta(4)-C4Ph4)Co[eta(5)-C5H4C(R)=C(Ar)Ar'], where R = Me or Et, and Ar = Ar' = p-C6H4X where X is OH, 2a and 2b, OMe, 2c and 2d, OBn, 2e and 2f, or O(CH2)(2)NMe2, 12a and 12b, and where Ar = C6H4OH and Ar' = C6H4O(CH2)(2)NMe2, 2g and 2h, have been characterised by NMR spectroscopy and/or X-ray crystallography. The effect of 2a and 2b, 2g and 2h, and 12a and 12b on the growth of MCF-7 (hormone-dependent) and MDA-MB-231 (hormone-independent breast cancer cells) was studied. The dihydroxycobaltifens 2a and 2b exhibit a strong estrogenic effect on MCF-7 cells while the aminoalkyl-hydroxycobaltifens, 2g and 2h, were found to be only slightly cytotoxic on MDA-MB-231 cells (IC50 = 27.5 and 17 mu M); surprisingly, however, the bis-(dimethylaminoethoxy) cobaltifens, 12a and 12b were shown to be highly cytotoxic towards both cell lines (IC50 = 3.8 and 2.5 mu M). (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.11.003