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1-(hydroxymethyl)-1,2-dicarba-closo-dodecaborane | 19610-34-5

中文名称
——
中文别名
——
英文名称
1-(hydroxymethyl)-1,2-dicarba-closo-dodecaborane
英文别名
(1'-hydroxymethyl)-1,2-dicarba-closo-dodecaborane;1-hydroxymethyl-2H-carborane;1-hydroxymethyl-o-carborane;1-methyloxy-ortho-carborane;o-C-carboranylmethanol;o-carboranyl methanol
1-(hydroxymethyl)-1,2-dicarba-closo-dodecaborane化学式
CAS
19610-34-5
化学式
C3H14B10O
mdl
——
分子量
174.254
InChiKey
DDSASUVXWHNRNP-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

SDS

SDS:2f1656d23fd0539fbe15cf95bc805676
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反应信息

  • 作为反应物:
    描述:
    1-(hydroxymethyl)-1,2-dicarba-closo-dodecaborane 在 Dess-Martin periodinane oxidant 作用下, 以 二氯甲烷 为溶剂, 以86%的产率得到1-formyl-o-carborane
    参考文献:
    名称:
    Synthesis, Structure, and Olefin Polymerization Behavior of Constrained-Geometry Group 4 Metallacarboranes Incorporating Imido-Dicarbollyl Ligands
    摘要:
    New imido-carboranes 1-(CH=NC6H3R2-2,6)-1,2-C2B10H11 (R = Pr-i (3a), Me (3b)) were successfully prepared by Schiff base condensation of 1-CHO-1,2-C2B10H11 with R2C6H3NH2. They were readily converted into the corresponding imido-dicarbollyl ligands 7-(CH=NHC6H3R2-2,6)-7,8-C2B9H11 (R = Pr-i (4a), Me (4b)) by refluxing in dry MeOH. Treatment of 3a with Ti(NMe2)(4) in hot toluene gave a constrained-geometry complex, [eta(1):eta(5)-((Pr2C6H3N)-Pr-i=CH)C2B9H10]Ti(NMe2)(2) (5a). Under the same reaction conditions, interaction of 3b with Ti(NMe2)(4) produced a mixture of [eta(1):eta(5)-(Me2C6H3N=CH)C2B9H10]Ti(NMe2)(2) (5b) and [eta(1):eta(5)-(Me2N)CH(NMe2)(C2B9H10)Ti(NMe2)(2) (8). Reaction of 4a with M(NMe2)(4) in toluene/DME at room temperature afforded 5a and [eta(1):eta(5)-((Pr2C6H3N)-Pr-i=CH)C2B9H10]M(NMe2)(2)(NHMe2) (M = Zr (6a), Hf (7a)), respectively. Complexes 5a, 6a, and 7a were active catalysts for the polymerization of ethylene in the presence of MMAO with activities of 3-16 kg/mol.h.atm. These new complexes were fully characterized by various spectroscopic techniques and elemental analyses. The molecular structures of 3a, 3b, 4a, 5a, 5b, 6a, 7a, and 8 were further confirmed by single-crystal X-ray analyses.
    DOI:
    10.1021/om060125y
  • 作为产物:
    描述:
    四丁基氟化铵 作用下, 以 乙醚 为溶剂, 反应 1.0h, 生成 1-(hydroxymethyl)-1,2-dicarba-closo-dodecaborane
    参考文献:
    名称:
    通过预先占位调控邻位碳硼烷衍生物结构的方法
    摘要:
    本发明公开了一种通过预先占位反应调控碳硼烷衍生物结构的方法,(1)邻碳硼烷经锂化形成单锂盐后与CH基团保护剂作用,定量转化为C‑H保护碳硼烷;(2)丁基锂活化C‑H进而进行第二碳位的官能化;(3)通过四丁基氟化铵脱保护。经三步法通过先引入以CH基团保护剂,再对基团进行官能化,最后进行基团的脱保护,通过预先占位调控邻位碳硼烷衍生物的结构,进而可有目的地,有选择性地合成单取代或双取代的邻位碳硼烷衍生物。得到的单取代或双取代碳硼烷衍生物也可引入耐高温粘结材料、复合材料等航空航天材料领域,也可以让其在生物医药、催化剂、超分子体系及高能燃料等领域均有较大的应用前景。
    公开号:
    CN106083905A
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文献信息

  • High Yielding Preparation of Dicarba-<i>closo</i>-dodecaboranes Using a Silver(I) Mediated Dehydrogenative Alkyne-Insertion Reaction
    作者:Antonio Toppino、Afaf R. Genady、Mohamed E. El-Zaria、James Reeve、Fargol Mostofian、Jeff Kent、John F. Valliant
    DOI:10.1021/ic400928v
    日期:2013.8.5
    The synthesis of 1,2-dicarba-closo-dodecaboranes (ortho-carboranes) is often low yielding which is a critical issue given the increasing use of boron clusters in material science and medicinal chemistry. To address this barrier, a series of Cu, Ag, and Au salts were screened to identify compounds that would enhance the yields of ortho-caboranes produced when treating alkynes with B10H12(CH3CN)2. Using
    合成1,2- dicarba-闭合碳-dodecaboranes(邻-carboranes)通常低产其是给定的在材料科学和药物化学越来越多地使用簇的一个关键问题。为了解决这一障碍,对一系列的盐进行了筛选,以鉴定出可提高用B 10 H 12(CH 3 CN)2处理炔烃时产生的邻环硼烷的收率的化合物。使用各种官能化的配体,包括单官能团和多官能团的内部和末端炔烃,当以催化量使用AgNO 3时,产率会显着提高。硝酸银3 似乎可以防止在碳硼烷形成之前炔烃的不希望的还原/氢化,并且该方法与芳基,卤素,羟基,腈,氨基甲酸酯和羰基官能化的炔烃兼容。
  • <sup>11</sup> B NMR Probes of Copper(II): Finding and Implications of the Cu <sup>2+</sup> ‐Promoted Decomposition of <i>ortho</i> ‐Carborane Derivatives
    作者:Tomohiro Tanaka、Yukiko Nishiura、Rikita Araki、Takaomi Saido、Ryo Abe、Shin Aoki
    DOI:10.1002/ejic.201600117
    日期:2016.4
    ) are decomposed in the presence of Mn2+ or Cu2+ in aqueous solution at neutral pH, accompanied by the release of 4–9 equiv. of B(OH)3. Furthermore, it was found that o-carborane derivatives that contain hydroxyl groups instead of a cyclen unit also undergo decomposition in the presence of Cu2+ and the corresponding complexes such as Cu(bpy) to afford 10 equiv. of B(OH)3, as confirmed by 11B NMR spectroscopic
    开发用于检测 (Cu2+)、 (Zn2+) 和 (Mn2+) 等 d 区属离子的无创方法对于了解它们的生物学作用和与疾病的关系非常重要。我们一直对使用 11B NMR 探针检测 d 区属离子很感兴趣,因为 11B 是生命系统中的一种超痕量元素。邻碳硼烷由十个和两个碳原子组成,已应用于多种药物和生物活性剂。在这项工作中,我们发现在 Mn2+ 或 Cu2+ 存在于中性 pH 值的溶液中时,邻碳硼烷悬链环(L3-L5)(cyclen = 1,4,7,10-四氮杂环十二烷)分解4-9 当量的释放。B(OH)3。此外,发现含有羟基而不是环单元的邻碳硼烷生物在 Cu2+ 和相应的配合物如 Cu(bpy) 存在下也会发生分解,得到 10 当量。B(OH)3,如 11B NMR 光谱分析和偶氮甲碱-H 分析所证实。这些反应适用于 Cu2+ 的 11B MRI(磁共振成像)探针。
  • Tetrabutylammonium Fluoride Promoted Novel Reactions of <i>o</i>-Carborane:  Inter- and Intramolecular Additions to Aldehydes and Ketones and Annulation via Enals and Enones
    作者:Hiroyuki Nakamura、Kouichi Aoyagi、Yoshinori Yamamoto
    DOI:10.1021/ja973832e
    日期:1998.2.1
    obtained in good-to-high yields. Further, [3 + 2] annulation between o-carborane (dianionic C2 synthons) and α,β-unsaturated aldehydes and ketones (dicationic C3 synthons) proceeded very smoothly in the presence of TBAF to give the corresponding five-membered carbocycles in good-to-high yields. Detailed mechanistic studies revealed that the [3 + 2] annulation proceeded through kinetically controlled 1,2-addition
    在室温下,在四丁基氟化铵溶液(TBAF;3 当量)的存在下,邻碳硼烷 (1) 向醛 2 的加成非常顺利,以高产率得到相应的甲醇 3。将 TBAF 介导的反应应用于邻碳醛和酮 4 的分子内环加成反应,并以良好到高的产率获得了相应的五元、六元和七元碳环。此外,在 TBAF 存在下,邻碳硼烷(双阴离子 C2 合成子)与 α,β-不饱和醛和酮(双阴离子 C3 合成子)之间的 [3 + 2] 环化进行得非常顺利,得到相应的五元碳环到高产量。详细的机理研究表明 [3 + 2] 环化是通过动力学控制的 1,2-加成和热力学控制的 1 进行的,
  • <i>ortho</i>-Carborane-Modified<i>N</i>-Substituted Deoxynojirimycins
    作者:Sascha Hoogendoorn、Elliot D. Mock、Anneke Strijland、Wilma E. Donker-Koopman、Hans van den Elst、Richard J. B. H. N. van den Berg、Johannes M. F. G. Aerts、Gijsbert A. van der Marel、Herman S. Overkleeft
    DOI:10.1002/ejoc.201500364
    日期:2015.7
    N-alkyl-deoxynojirimycins (DNMs) are an important class of glycoprocessing enzyme inhibitors. Our work on DNMs focuses on identifying potent and selective inhibitors of the human enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA) and neutral glucosylceramidase (GBA2). We have previously reported on N-alkylated DNM derivatives bearing various hydrophobic head groups (aliphatic
    N-烷基脱氧野尻霉素 (DNM) 是一类重要的糖加工酶抑制剂。我们在 DNM 方面的工作重点是鉴定人类酶、葡萄糖神经酰胺合成酶 (GCS)、溶酶体葡萄糖神经酰胺酶 (GBA) 和中性葡萄糖神经酰胺酶 (GBA2) 的有效和选择性抑制剂。我们之前曾报道过带有各种疏性头基(脂肪族、芳香族、支链、环状)的 N-烷基化 DNM 衍生物。在这项研究中,我们报告了合成邻碳硼烷修饰的 DNM 的有效程序,并确定了六种新的 DNM 衍生物 3-8 对 GCS、GBA 和 GBA2 的抑制效力。
  • High Yielding Synthesis of Carboranes Under Mild Reaction Conditions Using a Homogeneous Silver(I) Catalyst: Direct Evidence of a Bimetallic Intermediate
    作者:Mohamed E. El‐Zaria、Kunal Keskar、Afaf R. Genady、Joseph A. Ioppolo、James McNulty、John F. Valliant
    DOI:10.1002/anie.201311012
    日期:2014.5.12
    Methods used to prepare functionalized carboranes generally require heating to high temperatures, and thus limits the range of derivatives which can be prepared directly from alkynes. We show here that by using a homogeneous silver(I) catalyst it is now possible to prepare carboranes in good to excellent yield at temperatures below 40 °C, including at room temperature. The process is general and provides
    用于制备官能化碳硼烷的方法通常需要加热至高温,因此限制了可以直接从炔烃制备的衍生物的范围。我们在此表明​​,通过使用均相的(I)催化剂,现在可以在低于40°C的温度(包括室温)下以良好至极好的收率制备碳硼烷。该过程是常规过程,为功能化团簇的制备提供了重要的新合成策略。
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