[(Me5C5)Ir(η(5)-C10H11O)]BF4 | 188621-69-4

• 英文名称: [(Me5C5)Ir(η(5)-C10H11O)]BF4
• CAS: 188621-69-4
• 化学式: BF₄*C₂₀H₂₆IrO
• 分子量: 561.45
• InChiKey: ZYQLYPIRCCIYCX-UHFFFAOYSA-N

计算性质

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

• 作为反应物：
  描述：

  [(Me5C5)Ir(η(5)-C10H11O)]BF4 、 sodium hydride 在 MeOH 作用下， 以 甲醇 为溶剂， 以95%的产率得到[(C5Me5)Ir(η(4)-C10H11O(OMe))]
  参考文献：
  名称：

  Activation and Regioselective Ortho-Functionalization of the A-Ring of β-Estradiol Promoted by “Cp*Ir”:  An Efficient Organometallic Procedure for the Synthesis of 2-Methoxyestradiol

  摘要：

  5,6,7,8-Tetrahydro-2-naphthol (3) and beta-estradiol (1) gave eta(6)-arene complexes using [Cp*Ir-(solvent)(3)][BF4](2) (4) prepared in situ; subsequent O-deprotonation with NEt3 produced the corresponding complexes [Cp*Ir(oxo-eta(5)-dienyl)][BF4] (5 and 6a,b). In the case of the complexed hormone, the Cp*Ir moiety coordinates the A-ring either a (metal down, 6a) or beta (metal up, 6b) relative to the methyl group at C(13). The X-ray molecular structure of the cl-isomer 6a was determined. These (oxo-eta 5-dienyl)iridium derivatives 5 and 6a react with NaOMe in methanol at -40 degrees C to give respectively the novel iridium cyclohexadienone complexes [Cp*Ir(methoxy-eta(4)-dienone)] (7a and 8a) in 95 and 91% yields, respectively, with nucleophilic attack occurring exclusively at the ortho-position relative to the C=O function. The novel iridium cyclohexadienone compound of the complexed steroid 8a can be oxidized easily by iodine to produce 2-methoxyestradiol (2) in 60% overall yield from beta-estradiol. This efficient organometallic procedure is preferable to the classical organic procedure, which requires five steps and affords 2 in less than 5% yield.

  DOI：

  10.1021/om961079c
• 作为产物：
  描述：

  bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 5,6,7,8-四氢-2-萘酚 、 silver tetrafluoroborate 在 NEt₃ 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 以86%的产率得到[(Me5C5)Ir(η(5)-C10H11O)]BF4
  参考文献：
  名称：

  Activation and Regioselective Ortho-Functionalization of the A-Ring of β-Estradiol Promoted by “Cp*Ir”:  An Efficient Organometallic Procedure for the Synthesis of 2-Methoxyestradiol

  摘要：

  5,6,7,8-Tetrahydro-2-naphthol (3) and beta-estradiol (1) gave eta(6)-arene complexes using [Cp*Ir-(solvent)(3)][BF4](2) (4) prepared in situ; subsequent O-deprotonation with NEt3 produced the corresponding complexes [Cp*Ir(oxo-eta(5)-dienyl)][BF4] (5 and 6a,b). In the case of the complexed hormone, the Cp*Ir moiety coordinates the A-ring either a (metal down, 6a) or beta (metal up, 6b) relative to the methyl group at C(13). The X-ray molecular structure of the cl-isomer 6a was determined. These (oxo-eta 5-dienyl)iridium derivatives 5 and 6a react with NaOMe in methanol at -40 degrees C to give respectively the novel iridium cyclohexadienone complexes [Cp*Ir(methoxy-eta(4)-dienone)] (7a and 8a) in 95 and 91% yields, respectively, with nucleophilic attack occurring exclusively at the ortho-position relative to the C=O function. The novel iridium cyclohexadienone compound of the complexed steroid 8a can be oxidized easily by iodine to produce 2-methoxyestradiol (2) in 60% overall yield from beta-estradiol. This efficient organometallic procedure is preferable to the classical organic procedure, which requires five steps and affords 2 in less than 5% yield.

  DOI：

  10.1021/om961079c