[(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt] | 827303-96-8

• 英文名称: [(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]
• 英文别名: [(η⁵-propionylcyclopentadienyl)(η⁴-tetraphenylcyclobutadiene)cobalt]；[(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)]cobalt；(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt
• CAS: 827303-96-8
• 化学式: C₃₆H₂₉CoO
• 分子量: 536.619
• InChiKey: HYSUKUCRAXPJGV-UHFFFAOYSA-N

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：

  [(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt] 、 双(4-苯基甲氧基苯基)甲酮 在 TiCl₄ 、 Zn 作用下， 以 四氢呋喃 为溶剂， 以6.5%的产率得到1,1-bis(4-benzyloxyphenyl)-2-[(η5-cyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]-1-butene
  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benzophenones furnished a series of cobaltifens, organometallic analogues of tamoxifen whereby a phenyl ring has been replaced by an organo-cobalt sandwich moiety.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：

  cobalt,triphenylphosphane,chloride 、 丙酸甲酯 、 环戊二烯 、 二苯基乙炔 在 sodium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以11%的产率得到[(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt]
  参考文献：
  名称：

  的的McMurry反应（η 5 -acetylcyclopentadienyl）钴（η 4 -tetraphenylcyclobutadiene）与二苯甲酮：酮联接器和频哪醇/频哪酮重排

  摘要：

  的反应（η 4 -C 4博士4）有限公司[η 5 -C 5 H ^ 4 -C（O）Me]，5，用的McMurry条件下的二苯甲酮（的TiCl 4 /锌/ THF）给出异质偶联产物（η 4 -C 4博士4）有限公司[η 5 -C 5 H ^ 4 -C（Me）的器CPh 2 ]，7，与八羰基二种一起：反式- （η 4 -C 4博士4）钴[（η 5 -C 5 H 4-C（Me）的C（Me）的-η 5 -C 5 ħ 4- ）]的Co（η 4 -C 4博士4），9，和频哪酮我[（η 4 -C 4博士4）的Co（η 5 -C 5 H 4）] 2 C–C（O）Me，10。后者显然是从由频哪醇的迁移（η形成4 -C 4博士4）钴[（η 5 -C 5 H ^ 4） 团体。就涉及金属稳定阳离​​子的有利过渡态而言，合理化了钴夹心部分而不是甲基的优先迁移。产品7，9和10，并且也将酮（η 4 -C 4博士4）有限公司[η

  DOI：

  10.1016/j.jorganchem.2004.07.015
• 作为试剂：
  描述：

  4,4'-二甲氧基二苯甲酮 在 [(η5-propionylcyclopentadienyl)(η4-tetraphenylcyclobutadiene)cobalt] 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以15%的产率得到1,1,2,2-四(4-甲氧基苯基)乙烯
  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