(3R,4S)-non-1-ene-3,4-diol | 120190-60-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4S)-non-1-ene-3,4-diol
• 英文别名: (R,S)-non-1-ene-3,4-diol
• CAS: 120190-60-5
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: HDCRTDYFAHZMJM-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-non-1-ene-3,4-diol 在 二甲基硫 、 臭氧 作用下， 以 吡啶 为溶剂， 生成 [(2S,3S)-2-benzoyloxy-1-oxooctan-3-yl] benzoate
  参考文献：
  名称：

  Enantioselective synthesis of 1-vinyl-1,2-diols, vinyl epoxides and α,β-dialkoxy aldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(00)80846-1
• 作为产物：
  描述：

  (1E,3S)-1-cyano-1-octen-3-ol 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 bis(cyclopentadienyl)titanium (III) chloride 、 L-(+)-酒石酸二异丙酯 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 146.0h， 生成 (3R,4S)-non-1-ene-3,4-diol
  参考文献：
  名称：

  旋光性γ-氰基-β，γ-环氧醇和仲γ-氰基烯丙基醇的合成

  摘要：

  3-氰基烯丙基醇（4-羟基-2-丁烯腈，6）的Sharpless不对称环氧化提供了一种潜在有用的手性结构单元，3-cyano-2,3-epoxypropan-1-ol（7）。仲γ-氰基烯丙基醇（rac-3）的动力学拆分为合成旋光活性3提供了一种有效的方法。还报道了旋光性化合物3被环氧化为γ-氰基-α，β-环氧醇5。

  DOI：

  10.1016/s0040-4039(00)78904-0

文献信息

• ZrCl₄ as an Efficient Catalyst for a Novel One-Pot Protection/Deprotection Synthetic Methodology
  作者：Surendra Singh、Colm D. Duffy、Syed Tasadaque A. Shah、Patrick J. Guiry

  DOI：10.1021/jo800932t

  日期：2008.8.1

  found to be an efficient catalyst for the one-pot esterification and deprotection of (5S,6R)-5,6-diacetoxyoct-7-enoic acid in good yields (44−62%) with a lactone formed as a minor byproduct. ZrCl4 (10−20 mol %) was also sufficient to deprotect 1,3-dioxalane, bis-TBDMS ethers, and diacetate functional groups in excellent yields of up to 93%. ZrCl4 (1−10 mol %) also promoted diol protection as the acetonide

  发现催化量的ZrCl 4（20 mol％）是一种有效的催化剂，用于以高收率一锅法酯化和（5 S，6 R）-5,6-二乙酰氧基辛-7-烯酸脱保护（44 -62％），形成内酯为次要副产物。ZrCl 4（10-20 mol％）也足以以高达93％的优异收率对1,3-二氧杂戊环，bis-TBDMS醚和二乙酸酯官能团进行脱保护。ZrCl 4（1-10 mol％）还以90％的收率促进了作为丙酮化物的二醇保护作用，并充当了一系列酯的酯交换催化剂。
• A carbohydrate based approach towards the synthesis of aspercyclide C
  作者：C.V. Ramana、Mohabul A. Mondal、Vedavati G. Puranik、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2007.08.050

  日期：2007.10

  A formal total synthesis of aspercyclide C (3) is described in which d-ribose is employed as a chiral pool material. The key step is a ring closing metathesis.

  描述了正式的全合成的阿斯环素C（3），其中d-核糖用作手性库物质。关键步骤是闭环复分解。
• Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]- and (E)-γ-(dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective synthesis of anti 1,2-diols and 2-butene-1,4-diols via the formal α- and γ-hydroxyallylation of aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4020(01)88869-4

  日期：1992.1

  Enantioselective synthesis of 4-substituted (E)-2-butene-1,4-diols and anti 1,2-diols are described. Highly diastereoselective reactions of aldehydes and the chiral PhMe2Si- and (C6H11O)Me2Si- substituted allylboronates 25 and 26 provide anti homoallylic 29 and 50, respectively. Epoxidation of 29 with dimethyl dioxirane followed by acid catalyzed Petersen rearrangement of the intermediate epoxysilanols

  描述了4-取代的（E）-2-丁烯-1,4-二醇和抗1,2-二醇的对映选择性合成。醛与手性PhMe 2 Si-和（C 6 H 11 O）Me 2 Si-取代的烯丙基硼酸酯25和26的高度非对映选择性反应分别提供反均聚物29和50。29用二甲基二环氧乙烷环氧化，然后经酸催化的中间体环氧硅烷醇进行Petersen重排，可得到具有优异对映选择性（81-87％ee）的1,4-丁二醇27。Tamao氧化50提供抗二醇22（ee的64–72％）。这些程序尤其在与一系列氧化的手性醛进行双不对称反应时获得了优异的结果（图1和2）。这些方法有望用于非环状前体糖的非对映选择性合成中。
• Aromatic Lipoxin A₄ and Lipoxin B₄ Analogues Display Potent Biological Activities
  作者：Timothy P. O'Sullivan、Karl S. A. Vallin、Syed Tasadaque Ali Shah、Jérôme Fakhry、Paola Maderna、Michael Scannell、Andre L. F. Sampaio、Mauro Perretti、Catherine Godson、Patrick J. Guiry

  DOI：10.1021/jm060270d

  日期：2007.11.1

  aromatic LXA4 and LXB4 analogues by employing Sharpless epoxidation, Pd-mediated Heck coupling, and diastereoselective reduction as the key transformations. Subsequent biological testing has shown that these analogues display potent biological activities. Phagocytic clearance of apoptotic leukocytes plays a critical role in the resolution of inflammation. Both LXA4 analogues (1R)-3a and (1S)-3a were

  脂蛋白是一组通常通过跨细胞脂氧合酶活性形成的生物活性类花生酸。在多种炎症条件下均已检测到脂氧合蛋白A4（LXA4）和脂氧合蛋白B4（LXB4）的生物合成。天然脂毒素LXA4和LXB4表现出有效的抗炎和分解生物作用。然而，它们的治疗潜力受到PG脱氢酶介导的氧化和还原作用的快速代谢失活的影响。在这里，我们报告通过采用Sharpless环氧化，Pd介导的Heck偶联和非对映选择性还原作为关键转化，对芳香族LXA4和LXB4类似物进行立体选择性合成。随后的生物学测试表明，这些类似物显示出强大的生物学活性。凋亡性白细胞的吞噬清除在炎症消退中起关键作用。发现LXA4类似物（1R）-3a和（1S）-3a均能刺激巨噬细胞吞噬凋亡性多形核白细胞（PMN）的吞噬作用显着增加，其功效与天然LXA4相当，尽管效力更高，而LXB4类似物还刺激吞噬作用，在10-11 M时观察到最大作用。LX刺激的吞噬作用与肌动蛋白细
• 4,5-Diisopropyl-<i>B</i>-[(<i>E</i>)-[(3‘-menthofuryl)dimethylsilyl]allyl]-1,3,2- dioxaborolane, an Improved Chiral Reagent for the Anti α-Hydroxyallylation of Aldehydes:  Application to the Enantioselective Synthesis of (−)-Swainsonine
  作者：J. A. Hunt、William R. Roush

  DOI：10.1021/jo961840s

  日期：1997.2.1

  Diisopropyl tartrate-modified (E)-[gamma-(furyldimethylsilyl)allyl]boronates 10 and 11 were designed for the enantioselective synthesis of substituted anti-3,4-dihydroxy-1-butenes 9 via the anti-alpha-hydroxyallylation of aldehydes. The reactions of aldehydes with 10 and 11 provided furyldimethylsilyl-substituted anti-1,2-silanols 12 and 13 with good enantioselectivity (74-82% ee), and the silanols were oxidized to the corresponding anti-1,2-diols 9 by a modified Fleming-Tamao oxidation protocol. The high reactivity of the (menthofuryl)silane unit toward electrophilic substitution allowed complete protodesilylation of menthofuryl-substituted silanols 13 and subsequent oxidation to diols 9 in a one-pot operation without competing protodesilylation of the allylsilane unit. However, a two-step protocol was required for the protodesilylation-oxidation of the less reactive 2-(5-methyl)-asymmetric reactions with three chiral aldehydes 23-35 (80 to >92% de, with the exception of the mismatched reactions with aldehyde 25, which were essentially unselective). However, [[[2-(5-methylfuryl)]dimethylsilyl]ally]boronate 10 could only be synthesized in less than or equal to 15% yield, and oxidations of the 2-(5-methylfuryl)-substituted silanols 12 were lower-yielding than oxidations of the corresponding menthofuryl-substituted silanols 13. Thus diisopropyl tartrate-modified (E)-[gamma-[(menthofuryl)dimethylsilyl]ally]boronate 11 proved to be the more useful of the two reagents. As a demonstration of the utility of 11 in the synthesis of polyhydroxylated natural products, this new reagent was used in a brief and highly stereoselective synthesis of the naturally occurring alkaloid (-)-swainsonine (42).