(R)-1-(t-Butyldimethylsilyl)oxy-4-iodo-2-methylbutane | 147915-57-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-1-(t-Butyldimethylsilyl)oxy-4-iodo-2-methylbutane
• 英文别名: (R)-4-(tert-butyldimethylsilyloxy)-3-methylbutyl iodide；(R)-4-tert-butyldimethylsilyloxy-3-methyl-1-butyl iodide；(2S)-(+)-(tert-Butyldimethyl)-(3-iodo-2-methylpropoxy)silane；(R)-1-tert-butyldimethylsilyloxy-4-iodo-2-methylbutane；(R)-tert-butyl(4-iodo-2-methylbutoxy)dimethylsilane；tert-butyl-[(2R)-4-iodo-2-methylbutoxy]-dimethylsilane
• CAS: 147915-57-9
• 化学式: C₁₁H₂₅IOSi
• 分子量: 328.309
• InChiKey: RWNJAGKFEUACNZ-SNVBAGLBSA-N

物化性质

• 沸点：
  267.3±23.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-1-(t-Butyldimethylsilyl)oxy-4-iodo-2-methylbutane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 叔丁基锂 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 16.22h， 生成 (2R,7S,5E)-1,7-di((tert-butyldimethylsilyl)oxy)-2,5,8,8-tetramethylnon-5-ene
  参考文献：
  名称：

  Janadolide及其简化类似物的总合成和抗胰蛋白酶活性。

  摘要：

  Janadolide是从海洋蓝藻Okeania sp分离出的一种环状二肽天然产物。在这里，我们通过有效的固相策略描述了janadolide的总合成以及八个简化的类似物。天然产物的合成至关重要的是通过对映选择性（-）- B-氯二异opinocampheylborane介导的还原反应和B-烷基铃木反应来构建关键的聚酮化合物片段。Janadolide和简化的类似物对病原性布氏锥虫罗得氏菌和克氏锥虫具有抗锥虫活性。

  DOI：

  10.1021/acs.orglett.0c00840
• 作为产物：
  描述：

  (R)-4-tert-butyldimethylsilyloxy-3-methyl-1-butanol 在 吡啶 、 碳酸氢钠 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 (R)-1-(t-Butyldimethylsilyl)oxy-4-iodo-2-methylbutane
  参考文献：
  名称：

  New Syntheses of the Rice Moth and Stink Bug Pheromones by Employing (2R, 6S)-7-Acetoxy-2,6-dimethyl-1-heptanol as a Building Block

  摘要：

  以(2R, 6R, 10R)-7-乙酰氧基-2,6-二甲基-1-庚醇作为米蛾的雌性信息素，合成了(2R, 6R, 10R)-6,10,14-三甲基-2-十五烷醇和(2R, 6R, 10R)-2,6,10-三甲基十三酸甲酯、通过使用 (2R, 6S)-7-acetoxy-2,6-dimethyl-1-heptanol 作为共同的手性结构单元，合成了臭虫（Euschistus heros）的雄性信息素。

  DOI：

  10.1271/bbb.64.1713

文献信息

• A diene-transmissive approach to the quassinoid skeleton
  作者：Claude Spino、Bryan Hill、Pascal Dubé、Stéphane Gingras

  DOI：10.1139/v02-196

  日期：2003.1.1

  Several tetracyclic molecules were prepared by diene-transmissive Diels–Alder cycloadditions. Control over the stereochemical outcome of the cycloaddition was achieved and the structural features of the precursors affecting the stereochemistry is discussed. Useful information was gathered concerning the factors governing this stereocontrol, which will be indispensable for the future of this strategy

  几个四环分子是通过二烯传递的 Diels??Alder 环加成反应制备的。实现了对环加成立体化学结果的控制，并讨论了影响立体化学的前体的结构特征。收集了有关控制这种立体控制的因素的有用信息，这对于该策略的未来是必不可少的。关键词：类苦参素，抗癌剂，二烯传递 Diels??Alder 环加成，氧二烯，杂 Diels??Alder。
• Enantioselective synthesis of (1S,3S,7R)-3-methyl-α-himachalene, the sex pheromone of the sandfly Lutzomyia longipalpis from Jacobina, Brazil
  作者：Kenji Mori、Takuya Tashiro、Satoshi Sano

  DOI：10.1016/s0040-4039(00)00831-5

  日期：2000.7

  (1S,3S,7R)-3-Methyl-α-himachalene, the sex pheromone of the male sandfly (Lutzomyia longipalpis) from Jacobina, Brazil, was synthesized enantioselectively by employing Evans’ or Oppolzer’s asymmetric methylation as the key step. The absolute configuration at the ring junction of this pheromone is opposite to that of the known (1R,7R)-α-himachalene of plant origin.

  （1 S，3 S，7 R）-3-甲基-α-himachalene，来自巴西雅可比那的雄性fly（Lutzomyia longipalpis）的性信息素，是利用Evans或Oppolzer的不对称甲基化作为关键步骤选择性合成的。该信息素的环连接处的绝对构型与植物来源的已知（1 R，7 R）-α-喜马林烯的构型相反。
• Pheromone Synthesis, CCVIII: Synthesis of (1S,3S,7R)-3-Methyl-α-himachalene, the Sex Pheromone of the Sandfly Lutzomyia longipalpis from Jacobina, Brazil
  作者：Takuya Tashiro、Masahiko Bando、Kenji Mori

  DOI：10.1055/s-2000-8220

  日期：——

  (1S,3S,7R)-3-Methyl-α-himachalene, the sex pheromone of the male sandfly (Lutzomyia longipalpis) from Jacobina, Brazil, was synthesized enantioselectively by employing Evan's or Oppolzer's asymmetric methylation and intramolecular Diels-Alder reaction as the two key steps. The absolute configuration of the product was unambiguously established by X-ray analysis of a compound related to one of the synthetic intermediates. The ring junction of this sandfly pheromone possesses the absolute configuration opposite to that of the known (1R,7R)-α-himachalene of plant origin.

  (通过采用 Evan 或 Oppolzer 的不对称甲基化和分子内 Diels-Alder 反应这两个关键步骤，对映体选择性地合成了 (1S,3S,7R)-3-甲基-δ-himachalene，它是巴西雅各比纳雄性沙蝇（Lutzomyia longipalpis）的性信息素。通过对与合成中间体之一相关的化合物进行 X 射线分析，明确确定了产物的绝对构型。这种沙蝇信息素的环结具有与已知植物来源的(1R,7R)-δ-himachalene相反的绝对构型。
• Constructing Conformationally Constrained Macrobicyclic Musks
  作者：Philip Kraft、Riccardo Cadalbert

  DOI：10.1002/1521-3765(20010803)7:15<3254::aid-chem3254>3.0.co;2-#

  日期：2001.8.3

  To investigate the structure odor correlation of musks,(12R)-12-methyl-13-tridecanotide (1), a macrocyclic musk, and 13-tridecanolide. its non-musky demethyl analogue. were conformationally constrained by introduction of methylene bridges between C-3 and C-8 or C-9. These [7.5.1]- and [8.4.1]macrobicycles were synthesized starting from bicyclo[5.3.1]undec-8-en-9-one (3) and bicyclo[4.3.1]dec-7-en-8-one (8), respectively, by a sequence consisting of catalytic hydrogenation. a-alkylation with a TBS-protected (tert-butyldimethylsilyl) hydroxy halide., acid-catalyzed cyclization, oxidative cleavage of the formed enol ether double bond, and subsequent reduction of the carbonyl group via its tosylhydrazone. The compound (1R,6R,9R)-(+)-6-methyl-4-oxa-bicyclo[7.5.1]pentadecan-3-one (22) was found to possess the most pronounced musk odor, and this was rationalized by a superposition analysis with the polycyclic aromatic musk odorant (4S,7R)-Galaxolide (2). In its (1S,6R,9S)-(+)stereoisomer-23 as well as in (1S,6R, 10R)-(+)-6-methyl-4-oxabicyclo-[8.4.1]pentadecan-3-one (18) the (6R)-methyl group seems to hinder the interaction with the musk receptor, while the demethyl compounds 7 and 12 showed only very faint odors.
• Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus
  作者：Naoto Katoh、Takashi Nakahata、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2008.07.023

  日期：2008.9

  Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.