(R)-3-hydroxybutyl-triphenylphosphonium iodide | 75419-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-hydroxybutyl-triphenylphosphonium iodide
• 英文别名: (3R)-3-hydroxybutyl-triphenylphosphonium iodide；(3R)-hydroxybutyl-triphenylphosphonium iodide；[(3R)-3-hydroxybutyl]-triphenylphosphanium;iodide
• CAS: 75419-20-4
• 化学式: C₂₂H₂₄OP*I
• 分子量: 462.31
• InChiKey: DWRHPZBSAXQQOK-FSRHSHDFSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxybutyl-triphenylphosphonium iodide 在 正丁基锂 、 sodium hydride 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 生成 (R)-4-(Triphenyl-λ⁵-phosphanylidene)-butan-2-ol
  参考文献：
  名称：

  大环内酯抗生素A26771B的立体特异性全合成和绝对构型

  摘要：

  通过使用D-葡萄糖作为手性来源描述了十六元大环内酯抗生素A26771B的总合成及其绝对构型。

  DOI：

  10.1016/s0040-4039(00)92751-5
• 作为产物：
  描述：

  (3R)-1-iodo-3-triethylsilyloxy-butane 、 三苯基膦 以 乙腈 为溶剂， 反应 48.0h， 以96%的产率得到(R)-3-hydroxybutyl-triphenylphosphonium iodide
  参考文献：
  名称：

  2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses

  摘要：

  这项发明揭示了19,26-去甲基-1α,25-二羟基维生素D3的2α-甲基和2β-甲基类似物以及其药用。这些化合物在体外表现出生物活性，可作为抗癌剂以及治疗银屑病等皮肤疾病，以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的用途。这些化合物在体内几乎没有钙调节活性，因此可用于治疗人类的自身免疫性疾病，以及继发性甲状旁腺功能亢进和肾性骨病。

  公开号：

  US20120283228A1

文献信息

• An efficient synthesis of (R)-(+)-recifeiolide and related macrolides by using enantiomerically pure (R)-(−)-5-methyl-2,2,2-triphenyl-1,2λ5-oxaphospholane
  作者：Kentaro Okuma、Syun-ichi Hirabayashi、Masaaki Ono、Kosei Shioji、Haruo Matsuyama、Hans J Bestmann

  DOI：10.1016/s0040-4020(98)00142-2

  日期：1998.4

  E-(R)-(+)-8-Dodece-11-olide, which is known as recifeiolide, was synthesized by a six-step reaction starting from (R)-(+)-propene oxide in a total yield of 53 %. The key step of this synthesis is the preparation of (R)-(−)-methyl 11-hydroxy-8-dodecenate using (R)-(−)-5-methyl-2,2,2-triphenyl-1,2λ5-oxaphospholane. Be using this method, enantiomerically pure 13- and 14-membered macrolides were also synthesized

  E-（R）-（+）-8-十二烷基十一内酯，称为累西柔内酯，是通过从（R）-（+）-环氧丙烷开始的六步反应合成的，总收率为53 ％。该合成的关键步骤是使用（R）-（-）-5-甲基-2,2,2-三苯基-1,2制备（R）-（-）-甲基11-羟基-8-十二烯酸酯λ 5 -oxaphospholane。通过使用该方法，还合成了对映体纯的13和14元大环内酯。
• Total synthesis of deacetyl-caloporoside, a novel inhibitor of the GABAA receptor ion channel
  作者：Kuniaki Tatsuta、Shohei Yasuda

  DOI：10.1016/0040-4039(96)00316-4

  日期：1996.4

  The total synthesis of deacetyl-caloporoside (1) which contains a β-d-mannopyranoside unit has been accomplished by coupling of the disaccharide-like segment derived from methyl α-d-mannopyranoside, with the hydroxyheptadecyl salicylic acid segment. The biological activity of 1 has also been evaluated.

  通过将衍生自甲基α-d-甘露吡喃糖苷的二糖样片段与羟基庚基水杨酸片段偶联，完成了包含β-d-甘露吡喃糖苷单元的脱乙酰-伞花苷（1）的全合成。还已经评估了1的生物活性。
• 2-Methylene-(20S,25R)-19,26-Dinor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170820A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25R)-19,26-dinor-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  该发明揭示了2-亚甲基-(20S,25R)-19,26-双去-维生素D类似物，具体为2-亚甲基-(20S,25R)-19,26-双去-1α,25-二羟基维生素D3，以及其药用。该化合物在抑制未分化细胞增殖和诱导它们分化为单核细胞方面表现出显著活性，因此可作为抗癌剂以及用于治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的药物。该化合物几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨病。该化合物还可用于治疗或预防肥胖。
• 2-Methylene-19,26-Dinor-(20R,22E,25R)-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20100009946A1

  公开（公告）日：2010-01-14

  This invention discloses 2-methylene-19,26-dinor-(20R,22E,25R)-vitamin D analogs, and specifically 2-methylene-19,26-dinor-(20R,22E,25R)-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows very low activity in vivo on bone calcium mobilization and relatively high intestinal calcium transport activity compared to the native hormone 1α,25-dihydroxyvitamin D 3 , and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  该发明揭示了2-亚甲基-19,26-二诺尔-(20R,22E,25R)-维生素D类似物，特别是2-亚甲基-19,26-二诺尔-(20R,22E,25R)-1α,25-二羟基维生素D3，以及其药用。该化合物表现出转录活性，并且在阻止未分化细胞增殖并诱导它们分化为单核细胞方面具有显著活性，从而表明其用作抗癌剂以及用于治疗银屑病等皮肤疾病以及皱纹、松弛的皮肤、干燥的皮肤和皮脂分泌不足等皮肤状况。该化合物在体内对骨钙动员的活性非常低，相对于天然激素1α,25-二羟基维生素D3具有较高的肠道钙运输活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨病变。该化合物还可用于肥胖的治疗或预防。
• 2-Methylene-19,26-Dinor-(20S,22E,25R)-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20100009947A1

  公开（公告）日：2010-01-14

  This invention discloses 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs, and specifically 2-methylene-19,26-dinor-(20S,22E,25R)-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows no activity in vivo on bone calcium mobilization and relatively low intestinal calcium transport activity compared to the native hormone 1α,25-dihydroxyvitamin D 3 , and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  该发明披露了2-亚甲基-19,26-去甲-(20S,22E,25R)-维生素D类似物，具体为2-亚甲基-19,26-去甲-(20S,22E,25R)-1α,25-二羟基维生素D3，以及其药用用途。该化合物表现出转录活性，以及在阻止未分化细胞增殖和诱导它们分化为单核细胞方面表现出显著活性，因此可作为抗癌剂和用于治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的药物。该化合物在体内对骨钙动员没有活性，与天然激素1α,25-二羟基维生素D3相比，肠钙运输活性相对较低，因此可用于治疗人类的自身免疫性疾病或炎症性疾病，以及肾性骨病。该化合物还可用于治疗或预防肥胖症。