1-(3'-iodopropyl)-1,2-dicarba-closo-dodecaborane | 23868-53-3

• 英文名称: 1-(3'-iodopropyl)-1,2-dicarba-closo-dodecaborane
• 英文别名: 1-(3-iodopropyl)-o-carborane；1-(CH2)3I-1.2-C2B10H11；1-iodopropyl-closo-1,2-C2B10H11
• CAS: 23868-53-3
• 化学式: C₅H₁₇B₁₀I
• 分子量: 312.204
• InChiKey: WFZICCZKTNJNFP-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：
  None
• 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：

  1-(3'-iodopropyl)-1,2-dicarba-closo-dodecaborane 在 N(CH₃)2CH₂C₆H₄NH₂ 作用下， 以 苯 为溶剂， 以92-97的产率得到1-{(CH₂)3N(CH₃)2CH₂C₆H₄NH₂}I-1.2-C₂B₁₀H₁₁
  参考文献：
  名称：

  Wong, H. S.; Tolpin, E. I.; Lipscomb, W. N., Journal of Medicinal Chemistry, 1974, vol. 17, p. 785 - 791

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3'-chloropropyl)-1,2-dicarba-closo-dodecaborane 、 sodium iodide 以 丙酮 为溶剂， 以96%的产率得到1-(3'-iodopropyl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  The preparation and characterization of functionalized carboranes and Re/Tc-metallocarboranes as platforms for developing molecular imaging probes: Structural and cage isomerism studies

  摘要：

  A study of the structure and reactivity of a series of carborane ligands [(RC2B9H11)(-)] towards Re(I) and Tc-99m(I) was undertaken in which the arising products [(M(CO)(3)RC2B9H10)(-), M = Re, Tc-99m] can be used as platforms to develop organometallic molecular imaging agents. Synthetic methods are reported that produce good yields of the target ligands and metal complexes where the organometallic complexes were prepared in aqueous solvents at both the macroscopic scale and at the tracer level. NMR and X-ray crystallography studies confirmed the structures of the closo and nido-ligands and demonstrated that the rhenacarborane complexes exist as 3,1,2 and/or 2,1,8 isomers where the product distribution depends upon on the steric bulk and electronic influence of the substituent linked to the carbon atom of the carborane cage. Experiments at the tracer level with Tc-99m(I) demonstrated for one ligand a difference in the ratio of isomers produced and the reactivity of the ligands compared to that for Re(I). Data is also presented to show for the first time that a 3,1,2-technetium carborane forms initially during radiolabeling and then upon heating isomerizes to the more stable 2,1,8 isomer. The comparable process is not observed for rhenium. The log D values for the technetium complexes were also measured and are within the range needed to cross the blood-brain-barrier making the reported compounds viable candidates for imaging key targets in the central nervous system. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.017

文献信息

• Carbaborane-functionalised 2,2′:6′,2″-terpyridine ligands for metallosupramolecular chemistry: Syntheses, complex formation, and the crystal and molecular structures of 4′-(ortho-carboranyl)-2,2′:6′,2″-terpyridine and 4′-(ortho-carboranylpropoxy)-2,2′:6′,2″-terpyridine1This paper is dedicated to Professor Ken Wade on the occasion of his 65th birthday.1
  作者：Dominique Armspach、Edwin C. Constable*、Catherine E. Housecroft、Markus Neuburger、Margareta Zehnder

  DOI：10.1016/s0022-328x(97)00238-6

  日期：1998.1

  A series of functionalised 2,2′:6′,2″-terpyridine ligands, each with a closo-1,2-C2B10H10R (R=H or SitBuMe2) substituent in the 4′ position, either directly or indirectly attached to the heterocyclic ring, has been prepared; two members of the series, 4′-(3-ortho-carboranylpropoxy)-2,2′:6′,2″-terpyridine (4) and 4′-(ortho-carboranyl)-2,2′:6′,2″-terpyridine (7) have been characterised by X-ray crystallography

  一系列官能化2,2'：6'，2“ -三联吡啶配体，每一个闭合碳-1,2--C 2乙10 ħ 10 R（R = H或Si吨BuMe 2）的取代基在4'位已经制备了直接或间接连接到杂环上的化合物；该系列的两个成员4'-（3-邻-甲碳烷基丙氧基）-2,2'：6'，2 ''-吡啶（4）和4'-（（邻-甲碳烷基）-2,2'：6'，X射线晶体学表征了2″-叔吡啶（7）。配体（反应7）与醇导致的硼脱帽closo-笼并产生两性离子氨基-簇官能化的配体。在三联吡啶结构域与钌（II）配位的配合物中，已观察到了碳甲环笼的类似变化。然而，如果在Si不发生脱帽吨BuMe 2 -保护的carbaborane笼被并入三联吡啶配体。
• Synthesis of novel boron-containing polyamines—Agents for DNA targeting in Neutron Capture Therapy
  作者：Joya R. Hariharan、Iwona M. Wyzlic、Albert H. Soloway

  DOI：10.1016/0277-5387(94)00497-3

  日期：1995.3

  A new class of carriers for Neutron Capture Therapy, boronated polyamines, are presented that may possess a high affinity for DNA and rapid/specific uptake in brain tumors by comparison with adjacent normal brain. Two first boron-containing polyamines such as 1,8-diamino-4-(4-o-carboranylbutyl)-4-azaoctane and 1,8-diamino-4-(3-o-carbonylpropyl)-4-azaoctane were synthesized via silylation-alkylation

  提出了一种用于中子俘获治疗的新型载体，硼化多胺，与相邻的正常大脑相比，它们对DNA具有很高的亲和力，并且在脑肿瘤中具有快速/特异性摄取的能力。通过以下方法合成了两个第一批含硼的多胺，例如1,8-二氨基-4-（4-邻碳硼烷基丁基）-4-氮杂辛烷和1,8-二氨基-4-（3-邻羰基丙基）-4-氮杂辛烷。双-Boc保护的亚精胺与碳硼烷基碘化物或甲苯磺酸盐的甲硅烷基化-烷基化反应。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.11, 4.5.1, page 189 - 199
  作者：

  DOI：——

  日期：——
• Synthesis of <i>Ortho</i>- and <i>Meta</i>-Re(I)-Metallocarboranes in Water
  作者：Oyebola O. Sogbein、Andrew E. C. Green、Paul Schaffer、Raymond Chankalal、Edwin Lee、Brian D. Healy、Pierre Morel、John F. Valliant

  DOI：10.1021/ic0511221

  日期：2005.12.1

  A series of metallocarboranes of the types rac[M(CO)(3)(n(5)-7-R-7,8-C2B9H11)](-)and rac-[M(CO)(3)(n(5)-7-R-8-R'-7,8-C2B9H11)](-), and rac-[M(CO)(3)(n(5)-7-R-7,9-C2B9H11)](-) (M = Re) were prepared by reacting [NEt4](2)[Re(CO)(3)Br-3] or [Re(CO)(3-)(OH2)(3)]Br with the corresponding carboranes in the presence of aqueous solutions of either alkali metal or tetraalkylammonium fluoride salts. Carborane derivatives that were investigated included those containing pyridine, amino, carboxylic acid, carbohydrate, and aryl substituents, During the course of the research, it was discovered that Re metallocarboranes can be prepared directly from the respective closo-clusters under similar reaction conditions used with nido-carboranes. Reaction yields ranged from modest to excellent depending on the carborane isomer and the nature of the cage substituent(s). A crystal structure of an amine-substituted Re metal locarborane was obtained where the complex crystallized in the orthorhombic space group P2(1)2(1)2(1) with a = 8.982(2) angstrom, b 11.563(3) angstrom, c = 16.811(4) angstrom, (alpha = beta = gamma = 90 degrees, V = 1746.1(7) angstrom(3), Z = 4, and R1 = 0.0684.