3-Methyl-pentantriol-(1,2,5) | 1114-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-pentantriol-(1,2,5)
• 英文别名: 3-Methyl-pentan-triol-(1,3,5)；(2S,3R)-3-methyl-pentane-1,2,5-triol；(2S,3R)-3-methylpentane-1,2,5-triol
• CAS: 1114-84-7；72692-98-9；73744-63-5
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: XCUKPLKWHIBYLO-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-Methyl-pentantriol-(1,2,5) 在 N-methyl-N,N'-dicyclohexylcarbodiiminium methyl iodide 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 <4S-<1R>>-(+)-4-<3-iodo-1-methylpropyl>-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Boeckman Jr., Robert K.; Charette, André B.; Asberom, Theodros, Journal of the American Chemical Society, 1991, vol. 113, # 14, p. 5337 - 5353

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-(+)-4-(2-carbomethoxy-1-ethynyl)-2,2-dimethyl-1,3-dioxolane 在 Rh/Al₂O₃ 盐酸 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 氢气 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 36.67h， 生成 3-Methyl-pentantriol-(1,2,5)
  参考文献：
  名称：

  Boeckman Jr., Robert K.; Charette, André B.; Asberom, Theodros, Journal of the American Chemical Society, 1991, vol. 113, # 14, p. 5337 - 5353

  摘要：

  DOI：

文献信息

• Über die Verrucarine und Roridine. 2. (vorläufige) Mitteilung. Partialstruktur von Verrucarin A
  作者：Ch. Tamm、J. Gutzwiller

  DOI：10.1002/hlca.19620450539

  日期：——

  The base catalysed hydrolysis of the antibiotic verrucarin A (C27H34O9) yields three products: (1) verrucarol (C15H22O4), a new sesquiterpene which is probably bicyclic, (2) muconic acid (C6H6O4), a new sesquiterpene which is probably bicyclic, (2) muconic acid (C6H6O4; cis,cis or cis, trans) and (3) verrucarinolactone (C6H10O3), the δ-lactone of the hitherto unknown trans-α,δ-dihydroxy-β-methylvaleric

  抗生素维鲁卡林A（C 27 H 34 O 9）的碱催化水解产生三种产物：（1）维鲁卡罗（C 15 H 22 O 4），一种可能是双环的新倍半萜，（2）粘康酸（C 6 H 6 O 4），一种新的倍半萜，可能是双环的；（2）粘康酸（C 6 H 6 O 4；顺式，顺式或顺式，反式）和（3）紫丁香内酯（C 6 H 10 O 3）），是迄今为止未知的反式α，δ-二羟基-β-甲基戊酸的δ-内酯。Verrucarinolactone的绝对构型由其与（R）-（+）-甲基琥珀酸的相关性推导。芦丁酸代表甲羟戊酸的新的天然异构体。
• Biosynthesis of the Verrucarins and Roridins. Part 1. The transformation of mevalonic acid into verrucarinic acid. Evidence for a hydrogen 1,2-shift. Verrucarins and roridins, 27th communication
  作者：Roland Achini、Beat Müller、Christoph Tamm

  DOI：10.1002/hlca.19740570520

  日期：1974.7.17

  AbstractIncorporation experiments using sodium [2‐14C]‐, [2‐3H]‐, (3R)‐[5‐14C]‐ and [2‐3H, 2‐14C]‐mevalonates and with mevalonates stereospecifically tritiated at C(2) demonstrate the transformation of mevalonic acid (8) into verrucarinic acid (5). Degradation experiments showed that this transformation occurs with a hydrogen 1, 2‐shift of the ‘pro‐2R’ hydrogen atom of mevalonate to C(3) of verrucarinate. A possible mechanistic pathway is discussed.
• Structural corrections of photinides A, B and their novel derivatives
  作者：Ryoko Yasumura、Kazuaki Tanaka、Tatsuo Nehira、Masaru Hashimoto

  DOI：10.1016/j.tet.2012.06.108

  日期：2012.9

  Stereochemistries of the C2=C8 double bond in photinides A and B were corrected to be reversed forms. The present studies also revised their absolute configurations by comparing the CD spectra of the degradation product with the corresponding synthetic sample. Discosia sp. SH 125 produced novel derivatives photinides X and Y, of which stereochemistry was established by NMR and CD analyses as well as theoretical calculations of the CD spectra. (C) 2012 Elsevier Ltd. All rights reserved.
• Über die Struktur von Verrucarin A. Verrucarine und Roridine, 5. Mitteilung
  作者：J. Gutzwiller、Ch. Tamm

  DOI：10.1002/hlca.19650480117

  日期：——

  AbstractThe antibiotic verrucarine A (C27H34O9) yields on base catalysed hydrolysis three products: (1) the sesquiterpene alcohol verrucarol (C15H22O4) (12), (2) cis, trans‐muconic acid (C6H6O4) (7), and (3) verrucarinolactone (C6H10O3) (9). The latter is the δ‐lactone of the hitherto unknown trans‐α, δ‐dihydroxy‐β‐methyl‐valeric acid (verrucarinic acid (16)). The absolute configuration of verrucarinolactone results from its degradation to (R)‐(+)‐methylsuccinic acid (21). Verrucarinolactone is a new natural isomer of mevalolactone.
• BOECKMAN, ROBERT K. (JR);CHARETTE, ANDRE B.;ASBEROM, THEODROS;JOHNSTON, B+, J. AMER. CHEM. SOC., 113,(1991) N, C. 5337-5353
  作者：BOECKMAN, ROBERT K. (JR)、CHARETTE, ANDRE B.、ASBEROM, THEODROS、JOHNSTON, B+

  DOI：——

  日期：——